# Electronic Supplementary Material (ESI) for ChemComm.
# 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_5tBuDACCl2_1a

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            5tBuDACCl2
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H18 Cl2 N2 O2'
_chemical_formula_sum            'C11 H18 Cl2 N2 O2'
_chemical_formula_weight         281.17

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 Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.3148(19)
_cell_length_b                   14.215(3)
_cell_length_c                   11.639(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.688(5)
_cell_angle_gamma                90.00
_cell_volume                     1356.1(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             592
_exptl_absorpt_coefficient_mu    0.471
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   none

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            19296
_diffrn_reflns_av_R_equivalents  0.0989
_diffrn_reflns_av_sigmaI/netI    0.0511
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.15
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2373
_reflns_number_gt                1924
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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/[σ²(Fo²)+(0.0476P)²+1.2874P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2373
_refine_ls_number_parameters     160
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0598
_refine_ls_R_factor_gt           0.0449
_refine_ls_wR_factor_ref         0.1055
_refine_ls_wR_factor_gt          0.0982
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_restrained_S_all      1.006
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
Cl1 Cl 0.48899(8) 0.08163(5) 0.36725(6) 0.0213(2) Uani 1 1 d . . .
O1 O 0.2822(2) 0.39393(13) 0.30572(17) 0.0232(5) Uani 1 1 d . . .
N1 N 0.3928(3) 0.25780(15) 0.39666(19) 0.0162(5) Uani 1 1 d . . .
C1 C 0.3372(3) 0.16215(18) 0.4000(2) 0.0164(6) Uani 1 1 d . . .
Cl2 Cl 0.29270(9) 0.13478(5) 0.54327(6) 0.0214(2) Uani 1 1 d . . .
O2 O 0.0270(2) 0.26648(13) 0.20382(18) 0.0256(5) Uani 1 1 d . . .
C2 C 0.2812(3) 0.31013(19) 0.3250(2) 0.0174(6) Uani 1 1 d . . .
N2 N 0.1911(3) 0.15601(15) 0.31422(18) 0.0157(5) Uani 1 1 d . . .
C3 C 0.1479(3) 0.24338(19) 0.2713(2) 0.0180(6) Uani 1 1 d . . .
C4 C 0.5395(3) 0.3032(2) 0.4726(2) 0.0213(6) Uani 1 1 d . . .
C5 C 0.6532(4) 0.2329(2) 0.5449(3) 0.0275(7) Uani 1 1 d . . .
H5A H 0.5912 0.1938 0.5887 0.041 Uiso 1 1 calc R . .
H5B H 0.7349 0.2663 0.5975 0.041 Uiso 1 1 calc R . .
H5C H 0.7049 0.1944 0.4940 0.041 Uiso 1 1 calc R . .
C6 C 0.6374(4) 0.3535(2) 0.3912(3) 0.0258(7) Uani 1 1 d . . .
H6A H 0.6749 0.3084 0.3402 0.039 Uiso 1 1 calc R . .
H6B H 0.7294 0.3844 0.4364 0.039 Uiso 1 1 calc R . .
H6C H 0.5694 0.3992 0.3457 0.039 Uiso 1 1 calc R . .
C7 C 0.4743(4) 0.3714(2) 0.5547(3) 0.0272(7) Uani 1 1 d . . .
H7A H 0.4159 0.3371 0.6056 0.041 Uiso 1 1 calc R . .
H7B H 0.4021 0.4157 0.5099 0.041 Uiso 1 1 calc R . .
H7C H 0.5637 0.4045 0.6002 0.041 Uiso 1 1 calc R . .
C8 C 0.0768(3) 0.07188(19) 0.2870(2) 0.0201(6) Uani 1 1 d . . .
C9 C -0.0781(4) 0.0945(2) 0.3359(3) 0.0272(7) Uani 1 1 d . . .
H9A H -0.1541 0.0434 0.3193 0.041 Uiso 1 1 calc R . .
H9B H -0.1263 0.1510 0.3006 0.041 Uiso 1 1 calc R . .
H9C H -0.0512 0.1031 0.4188 0.041 Uiso 1 1 calc R . .
C10 C 0.1503(4) -0.02005(19) 0.3398(3) 0.0264(7) Uani 1 1 d . . .
H10A H 0.0695 -0.0689 0.3269 0.040 Uiso 1 1 calc R . .
H10B H 0.1859 -0.0119 0.4221 0.040 Uiso 1 1 calc R . .
H10C H 0.2417 -0.0372 0.3037 0.040 Uiso 1 1 calc R . .
C11 C 0.0420(4) 0.0606(2) 0.1549(3) 0.0255(7) Uani 1 1 d . . .
H11A H -0.0298 0.0081 0.1347 0.038 Uiso 1 1 calc R . .
H11B H 0.1424 0.0498 0.1267 0.038 Uiso 1 1 calc R . .
H11C H -0.0086 0.1168 0.1201 0.038 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds 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
Cl1 C1 1.792(3) . ?
O1 C2 1.213(3) . ?
N1 C2 1.360(3) . ?
N1 C1 1.439(3) . ?
N1 C4 1.524(3) . ?
C1 N2 1.439(3) . ?
C1 Cl2 1.810(3) . ?
O2 C3 1.212(3) . ?
C2 C3 1.512(4) . ?
N2 C3 1.364(3) . ?
N2 C8 1.528(3) . ?
C4 C7 1.523(4) . ?
C4 C6 1.527(4) . ?
C4 C5 1.527(4) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C11 1.524(4) . ?
C8 C9 1.527(4) . ?
C8 C10 1.528(4) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?

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
C2 N1 C1 110.1(2) . . ?
C2 N1 C4 121.4(2) . . ?
C1 N1 C4 127.9(2) . . ?
N1 C1 N2 106.0(2) . . ?
N1 C1 Cl1 110.88(19) . . ?
N2 C1 Cl1 110.85(18) . . ?
N1 C1 Cl2 110.16(18) . . ?
N2 C1 Cl2 110.30(18) . . ?
Cl1 C1 Cl2 108.62(14) . . ?
O1 C2 N1 128.7(3) . . ?
O1 C2 C3 124.6(2) . . ?
N1 C2 C3 106.7(2) . . ?
C3 N2 C1 109.8(2) . . ?
C3 N2 C8 121.3(2) . . ?
C1 N2 C8 127.9(2) . . ?
O2 C3 N2 128.5(3) . . ?
O2 C3 C2 124.6(2) . . ?
N2 C3 C2 106.9(2) . . ?
C7 C4 N1 107.4(2) . . ?
C7 C4 C6 112.0(2) . . ?
N1 C4 C6 107.2(2) . . ?
C7 C4 C5 108.9(2) . . ?
N1 C4 C5 113.8(2) . . ?
C6 C4 C5 107.6(2) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C4 C6 H6A 109.5 . . ?
C4 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C4 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C11 C8 C9 111.7(2) . . ?
C11 C8 N2 107.3(2) . . ?
C9 C8 N2 107.0(2) . . ?
C11 C8 C10 108.1(2) . . ?
C9 C8 C10 109.6(2) . . ?
N2 C8 C10 113.2(2) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.307
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.064
_database_code_depnum_ccdc_archive 'CCDC 983770'
#######################################################################
#
#                 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_5AdDACCl2_1b

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            5AdDACCl2
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H30 Cl2 N2 O2'
_chemical_formula_sum            'C23 H30 Cl2 N2 O2'
_chemical_formula_weight         437.39

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 Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   14.331(4)
_cell_length_b                   11.335(4)
_cell_length_c                   12.768(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.063(6)
_cell_angle_gamma                90.00
_cell_volume                     2020.3(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.438
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             928
_exptl_absorpt_coefficient_mu    0.345
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   none

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13343
_diffrn_reflns_av_R_equivalents  0.0356
_diffrn_reflns_av_sigmaI/netI    0.0278
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.02
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3550
_reflns_number_gt                3314
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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/[σ²(Fo²)+(0.0475P)²+2.1207P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3550
_refine_ls_number_parameters     262
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0393
_refine_ls_R_factor_gt           0.0366
_refine_ls_wR_factor_ref         0.0958
_refine_ls_wR_factor_gt          0.0937
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_restrained_S_all      1.006
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
Cl1 Cl 0.10518(3) 0.24274(4) -0.05920(3) 0.01709(13) Uani 1 1 d . . .
O1 O 0.06871(9) 0.03553(12) 0.25569(10) 0.0189(3) Uani 1 1 d . . .
N1 N 0.05303(10) 0.17645(13) 0.12011(12) 0.0121(3) Uani 1 1 d . . .
C1 C 0.12054(13) 0.25181(15) 0.08433(14) 0.0124(4) Uani 1 1 d . . .
Cl2 Cl 0.10241(3) 0.40465(4) 0.11820(4) 0.01770(14) Uani 1 1 d . . .
O2 O 0.26985(9) 0.07905(12) 0.27768(10) 0.0177(3) Uani 1 1 d . . .
N2 N 0.21454(10) 0.21202(13) 0.13831(12) 0.0119(3) Uani 1 1 d . . .
C2 C 0.10073(12) 0.10412(15) 0.20025(14) 0.0124(4) Uani 1 1 d . . .
C3 C 0.20695(13) 0.12738(16) 0.21221(14) 0.0129(4) Uani 1 1 d . . .
C4 C 0.31002(12) 0.26811(16) 0.13500(14) 0.0125(4) Uani 1 1 d . . .
C5 C 0.38072(13) 0.16868(16) 0.12401(15) 0.0157(4) Uani 1 1 d . . .
H5A H 0.3846 0.1122 0.1819 0.019 Uiso 1 1 calc R . .
H5B H 0.3583 0.1277 0.0563 0.019 Uiso 1 1 calc R . .
C6 C 0.48032(13) 0.22212(17) 0.12851(16) 0.0178(4) Uani 1 1 d . . .
H6A H 0.5254 0.1587 0.1226 0.021 Uiso 1 1 calc R . .
C7 C 0.51569(13) 0.28730(18) 0.23524(15) 0.0184(4) Uani 1 1 d . . .
H7A H 0.5789 0.3197 0.2385 0.022 Uiso 1 1 calc R . .
H7B H 0.5201 0.2327 0.2947 0.022 Uiso 1 1 calc R . .
C8 C 0.44568(13) 0.38720(17) 0.24443(15) 0.0184(4) Uani 1 1 d . . .
H8A H 0.4686 0.4293 0.3124 0.022 Uiso 1 1 calc R . .
C9 C 0.34600(13) 0.33495(17) 0.24128(15) 0.0158(4) Uani 1 1 d . . .
H9A H 0.3495 0.2815 0.3014 0.019 Uiso 1 1 calc R . .
H9B H 0.3016 0.3978 0.2474 0.019 Uiso 1 1 calc R . .
C10 C 0.47457(13) 0.30831(19) 0.03544(15) 0.0204(4) Uani 1 1 d . . .
H10A H 0.4531 0.2674 -0.0325 0.024 Uiso 1 1 calc R . .
H10B H 0.5374 0.3415 0.0375 0.024 Uiso 1 1 calc R . .
C11 C 0.43908(14) 0.47291(17) 0.15082(16) 0.0221(4) Uani 1 1 d . . .
H11A H 0.3948 0.5361 0.1563 0.027 Uiso 1 1 calc R . .
H11B H 0.5015 0.5074 0.1531 0.027 Uiso 1 1 calc R . .
C12 C 0.30466(13) 0.35282(18) 0.03985(15) 0.0182(4) Uani 1 1 d . . .
H12A H 0.2588 0.4151 0.0427 0.022 Uiso 1 1 calc R . .
H12B H 0.2834 0.3104 -0.0273 0.022 Uiso 1 1 calc R . .
C13 C 0.40427(13) 0.40665(18) 0.04516(16) 0.0196(4) Uani 1 1 d . . .
H13A H 0.4001 0.4618 -0.0148 0.023 Uiso 1 1 calc R . .
C14 C -0.05553(12) 0.18991(16) 0.09578(14) 0.0120(4) Uani 1 1 d . . .
C15 C -0.09588(14) 0.26199(18) -0.00643(15) 0.0193(4) Uani 1 1 d . . .
H15A H -0.0812 0.2229 -0.0684 0.023 Uiso 1 1 calc R . .
H15B H -0.0668 0.3397 -0.0001 0.023 Uiso 1 1 calc R . .
C16 C -0.20547(13) 0.27325(18) -0.02117(16) 0.0203(4) Uani 1 1 d . . .
H16A H -0.2310 0.3215 -0.0849 0.024 Uiso 1 1 calc R . .
C17 C -0.25099(14) 0.15104(19) -0.03744(16) 0.0230(4) Uani 1 1 d . . .
H17A H -0.2368 0.1141 -0.1006 0.028 Uiso 1 1 calc R . .
H17B H -0.3200 0.1575 -0.0480 0.028 Uiso 1 1 calc R . .
C18 C -0.21021(14) 0.07580(18) 0.06283(17) 0.0226(4) Uani 1 1 d . . .
H18A H -0.2389 -0.0031 0.0534 0.027 Uiso 1 1 calc R . .
C19 C -0.10067(13) 0.06566(17) 0.07767(16) 0.0192(4) Uani 1 1 d . . .
H19A H -0.0857 0.0302 0.0143 0.023 Uiso 1 1 calc R . .
H19B H -0.0745 0.0157 0.1390 0.023 Uiso 1 1 calc R . .
C20 C -0.08115(13) 0.24711(17) 0.19424(15) 0.0173(4) Uani 1 1 d . . .
H20A H -0.0523 0.3248 0.2059 0.021 Uiso 1 1 calc R . .
H20B H -0.0563 0.1996 0.2575 0.021 Uiso 1 1 calc R . .
C21 C -0.22868(14) 0.33260(18) 0.07671(16) 0.0226(4) Uani 1 1 d . . .
H21A H -0.2975 0.3418 0.0662 0.027 Uiso 1 1 calc R . .
H21B H -0.1997 0.4103 0.0862 0.027 Uiso 1 1 calc R . .
C22 C -0.23352(14) 0.13443(19) 0.16180(16) 0.0236(4) Uani 1 1 d . . .
H22A H -0.3024 0.1393 0.1531 0.028 Uiso 1 1 calc R . .
H22B H -0.2078 0.0873 0.2251 0.028 Uiso 1 1 calc R . .
C23 C -0.19035(14) 0.25765(18) 0.17640(16) 0.0213(4) Uani 1 1 d . . .
H23A H -0.2065 0.2952 0.2392 0.026 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds 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
Cl1 C1 1.7986(19) . ?
O1 C2 1.209(2) . ?
N1 C2 1.368(2) . ?
N1 C1 1.440(2) . ?
N1 C14 1.524(2) . ?
C1 N2 1.440(2) . ?
C1 Cl2 1.8184(19) . ?
O2 C3 1.213(2) . ?
N2 C3 1.367(2) . ?
N2 C4 1.518(2) . ?
C2 C3 1.518(2) . ?
C4 C12 1.537(2) . ?
C4 C9 1.538(2) . ?
C4 C5 1.543(3) . ?
C5 C6 1.540(3) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C10 1.526(3) . ?
C6 C7 1.532(3) . ?
C6 H6A 0.9800 . ?
C7 C8 1.535(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C11 1.526(3) . ?
C8 C9 1.539(3) . ?
C8 H8A 0.9800 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C13 1.526(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C13 1.526(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.540(2) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9800 . ?
C14 C20 1.531(3) . ?
C14 C15 1.537(3) . ?
C14 C19 1.545(3) . ?
C15 C16 1.544(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C21 1.521(3) . ?
C16 C17 1.525(3) . ?
C16 H16A 0.9800 . ?
C17 C18 1.539(3) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C22 1.530(3) . ?
C18 C19 1.542(3) . ?
C18 H18A 0.9800 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 C23 1.534(3) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 C23 1.526(3) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 C23 1.522(3) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 H23A 0.9800 . ?

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
C2 N1 C1 109.57(14) . . ?
C2 N1 C14 121.82(14) . . ?
C1 N1 C14 127.16(14) . . ?
N2 C1 N1 106.58(14) . . ?
N2 C1 Cl1 110.83(12) . . ?
N1 C1 Cl1 110.67(12) . . ?
N2 C1 Cl2 110.68(12) . . ?
N1 C1 Cl2 110.32(12) . . ?
Cl1 C1 Cl2 107.80(9) . . ?
C3 N2 C1 109.78(14) . . ?
C3 N2 C4 121.73(14) . . ?
C1 N2 C4 127.38(14) . . ?
O1 C2 N1 129.18(17) . . ?
O1 C2 C3 123.86(16) . . ?
N1 C2 C3 106.93(14) . . ?
O2 C3 N2 129.05(16) . . ?
O2 C3 C2 124.26(16) . . ?
N2 C3 C2 106.67(14) . . ?
N2 C4 C12 113.53(14) . . ?
N2 C4 C9 107.83(14) . . ?
C12 C4 C9 109.68(15) . . ?
N2 C4 C5 108.13(14) . . ?
C12 C4 C5 107.52(15) . . ?
C9 C4 C5 110.12(14) . . ?
C6 C5 C4 109.37(15) . . ?
C6 C5 H5A 109.8 . . ?
C4 C5 H5A 109.8 . . ?
C6 C5 H5B 109.8 . . ?
C4 C5 H5B 109.8 . . ?
H5A C5 H5B 108.2 . . ?
C10 C6 C7 109.43(16) . . ?
C10 C6 C5 109.65(15) . . ?
C7 C6 C5 109.90(15) . . ?
C10 C6 H6A 109.3 . . ?
C7 C6 H6A 109.3 . . ?
C5 C6 H6A 109.3 . . ?
C6 C7 C8 109.47(15) . . ?
C6 C7 H7A 109.8 . . ?
C8 C7 H7A 109.8 . . ?
C6 C7 H7B 109.8 . . ?
C8 C7 H7B 109.8 . . ?
H7A C7 H7B 108.2 . . ?
C11 C8 C7 109.61(16) . . ?
C11 C8 C9 109.37(15) . . ?
C7 C8 C9 109.46(15) . . ?
C11 C8 H8A 109.5 . . ?
C7 C8 H8A 109.5 . . ?
C9 C8 H8A 109.5 . . ?
C4 C9 C8 109.68(15) . . ?
C4 C9 H9A 109.7 . . ?
C8 C9 H9A 109.7 . . ?
C4 C9 H9B 109.7 . . ?
C8 C9 H9B 109.7 . . ?
H9A C9 H9B 108.2 . . ?
C6 C10 C13 108.95(15) . . ?
C6 C10 H10A 109.9 . . ?
C13 C10 H10A 109.9 . . ?
C6 C10 H10B 109.9 . . ?
C13 C10 H10B 109.9 . . ?
H10A C10 H10B 108.3 . . ?
C13 C11 C8 109.21(16) . . ?
C13 C11 H11A 109.8 . . ?
C8 C11 H11A 109.8 . . ?
C13 C11 H11B 109.8 . . ?
C8 C11 H11B 109.8 . . ?
H11A C11 H11B 108.3 . . ?
C4 C12 C13 109.42(15) . . ?
C4 C12 H12A 109.8 . . ?
C13 C12 H12A 109.8 . . ?
C4 C12 H12B 109.8 . . ?
C13 C12 H12B 109.8 . . ?
H12A C12 H12B 108.2 . . ?
C11 C13 C10 109.96(16) . . ?
C11 C13 C12 110.39(16) . . ?
C10 C13 C12 109.24(16) . . ?
C11 C13 H13A 109.1 . . ?
C10 C13 H13A 109.1 . . ?
C12 C13 H13A 109.1 . . ?
N1 C14 C20 107.35(14) . . ?
N1 C14 C15 113.40(14) . . ?
C20 C14 C15 110.98(15) . . ?
N1 C14 C19 108.23(14) . . ?
C20 C14 C19 109.81(15) . . ?
C15 C14 C19 107.03(15) . . ?
C14 C15 C16 108.93(15) . . ?
C14 C15 H15A 109.9 . . ?
C16 C15 H15A 109.9 . . ?
C14 C15 H15B 109.9 . . ?
C16 C15 H15B 109.9 . . ?
H15A C15 H15B 108.3 . . ?
C21 C16 C17 110.33(16) . . ?
C21 C16 C15 109.98(16) . . ?
C17 C16 C15 109.48(16) . . ?
C21 C16 H16A 109.0 . . ?
C17 C16 H16A 109.0 . . ?
C15 C16 H16A 109.0 . . ?
C16 C17 C18 108.64(16) . . ?
C16 C17 H17A 110.0 . . ?
C18 C17 H17A 110.0 . . ?
C16 C17 H17B 110.0 . . ?
C18 C17 H17B 110.0 . . ?
H17A C17 H17B 108.3 . . ?
C22 C18 C17 109.48(17) . . ?
C22 C18 C19 109.69(16) . . ?
C17 C18 C19 109.15(17) . . ?
C22 C18 H18A 109.5 . . ?
C17 C18 H18A 109.5 . . ?
C19 C18 H18A 109.5 . . ?
C18 C19 C14 109.30(15) . . ?
C18 C19 H19A 109.8 . . ?
C14 C19 H19A 109.8 . . ?
C18 C19 H19B 109.8 . . ?
C14 C19 H19B 109.8 . . ?
H19A C19 H19B 108.3 . . ?
C14 C20 C23 109.68(15) . . ?
C14 C20 H20A 109.7 . . ?
C23 C20 H20A 109.7 . . ?
C14 C20 H20B 109.7 . . ?
C23 C20 H20B 109.7 . . ?
H20A C20 H20B 108.2 . . ?
C16 C21 C23 109.57(16) . . ?
C16 C21 H21A 109.8 . . ?
C23 C21 H21A 109.8 . . ?
C16 C21 H21B 109.8 . . ?
C23 C21 H21B 109.8 . . ?
H21A C21 H21B 108.2 . . ?
C23 C22 C18 109.95(16) . . ?
C23 C22 H22A 109.7 . . ?
C18 C22 H22A 109.7 . . ?
C23 C22 H22B 109.7 . . ?
C18 C22 H22B 109.7 . . ?
H22A C22 H22B 108.2 . . ?
C22 C23 C21 110.43(17) . . ?
C22 C23 C20 108.64(16) . . ?
C21 C23 C20 109.28(16) . . ?
C22 C23 H23A 109.5 . . ?
C21 C23 H23A 109.5 . . ?
C20 C23 H23A 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.506
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.059
_database_code_depnum_ccdc_archive 'CCDC 983771'
#######################################################################
#
#                 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_5tBuDAC_2a

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            5tBuDAC
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H18 N2 O2'
_chemical_formula_sum            'C11 H18 N2 O2'
_chemical_formula_weight         210.27

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 Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/n

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   13.3310(12)
_cell_length_b                   5.9383(5)
_cell_length_c                   15.6507(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.521(3)
_cell_angle_gamma                90.00
_cell_volume                     1193.78(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       plate
_exptl_crystal_colour            red-orange
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.170
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             456
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   none

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11792
_diffrn_reflns_av_R_equivalents  0.0416
_diffrn_reflns_av_sigmaI/netI    0.0286
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.17
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2089
_reflns_number_gt                1765
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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/[σ²(Fo²)+(0.0673P)²+0.5320P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2089
_refine_ls_number_parameters     142
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0546
_refine_ls_R_factor_gt           0.0452
_refine_ls_wR_factor_ref         0.1211
_refine_ls_wR_factor_gt          0.1137
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_restrained_S_all      1.006
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.47071(9) 0.1350(2) 0.32009(7) 0.0282(3) Uani 1 1 d . . .
O2 O 0.27098(9) 0.35901(19) 0.23743(7) 0.0290(3) Uani 1 1 d . . .
N2 N 0.29479(10) 0.1708(2) 0.11237(8) 0.0212(3) Uani 1 1 d . . .
N1 N 0.44156(10) -0.0057(2) 0.17507(8) 0.0220(3) Uani 1 1 d . . .
C2 C 0.42076(12) 0.1164(3) 0.24377(10) 0.0219(4) Uani 1 1 d . . .
C11 C 0.19818(14) 0.1344(3) -0.04462(11) 0.0331(4) Uani 1 1 d . . .
H11A H 0.1983 -0.0263 -0.0377 0.050 Uiso 1 1 calc R . .
H11B H 0.2587 0.1795 -0.0625 0.050 Uiso 1 1 calc R . .
H11C H 0.1367 0.1794 -0.0890 0.050 Uiso 1 1 calc R . .
C8 C 0.19952(12) 0.2459(3) 0.04287(10) 0.0237(4) Uani 1 1 d . . .
C1 C 0.36834(12) 0.0277(3) 0.09540(10) 0.0236(4) Uani 1 1 d . . .
C3 C 0.31734(12) 0.2350(3) 0.20040(10) 0.0217(4) Uani 1 1 d . . .
C10 C 0.10423(12) 0.1748(3) 0.07220(11) 0.0286(4) Uani 1 1 d . . .
H10A H 0.1053 0.2475 0.1272 0.043 Uiso 1 1 calc R . .
H10B H 0.1050 0.0145 0.0801 0.043 Uiso 1 1 calc R . .
H10C H 0.0423 0.2177 0.0278 0.043 Uiso 1 1 calc R . .
C4 C 0.53764(12) -0.1463(3) 0.18405(11) 0.0242(4) Uani 1 1 d . . .
C9 C 0.20369(14) 0.5016(3) 0.03435(12) 0.0331(4) Uani 1 1 d . . .
H9A H 0.2060 0.5699 0.0904 0.050 Uiso 1 1 calc R . .
H9B H 0.1429 0.5528 -0.0094 0.050 Uiso 1 1 calc R . .
H9C H 0.2648 0.5430 0.0167 0.050 Uiso 1 1 calc R . .
C5 C 0.52685(14) -0.2799(3) 0.09922(12) 0.0340(4) Uani 1 1 d . . .
H5A H 0.4650 -0.3705 0.0876 0.051 Uiso 1 1 calc R . .
H5B H 0.5865 -0.3756 0.1058 0.051 Uiso 1 1 calc R . .
H5C H 0.5222 -0.1781 0.0507 0.051 Uiso 1 1 calc R . .
C7 C 0.54837(15) -0.3087(3) 0.26136(12) 0.0366(5) Uani 1 1 d . . .
H7A H 0.4851 -0.3932 0.2533 0.055 Uiso 1 1 calc R . .
H7B H 0.5616 -0.2251 0.3158 0.055 Uiso 1 1 calc R . .
H7C H 0.6052 -0.4100 0.2638 0.055 Uiso 1 1 calc R . .
C6 C 0.63074(13) 0.0122(3) 0.20059(13) 0.0354(5) Uani 1 1 d . . .
H6A H 0.6231 0.1107 0.1506 0.053 Uiso 1 1 calc R . .
H6B H 0.6935 -0.0742 0.2088 0.053 Uiso 1 1 calc R . .
H6C H 0.6344 0.1001 0.2528 0.053 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds 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
O1 C2 1.2068(19) . ?
O2 C3 1.2048(19) . ?
N2 C1 1.376(2) . ?
N2 C3 1.383(2) . ?
N2 C8 1.5020(19) . ?
N1 C1 1.377(2) . ?
N1 C2 1.385(2) . ?
N1 C4 1.504(2) . ?
C2 C3 1.535(2) . ?
C11 C8 1.517(2) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C8 C10 1.521(2) . ?
C8 C9 1.527(2) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C4 C5 1.520(2) . ?
C4 C7 1.524(2) . ?
C4 C6 1.524(2) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?

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
C1 N2 C3 112.74(13) . . ?
C1 N2 C8 123.49(13) . . ?
C3 N2 C8 123.77(13) . . ?
C1 N1 C2 112.78(13) . . ?
C1 N1 C4 122.98(13) . . ?
C2 N1 C4 124.10(13) . . ?
O1 C2 N1 130.11(15) . . ?
O1 C2 C3 126.01(14) . . ?
N1 C2 C3 103.86(12) . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N2 C8 C11 109.12(13) . . ?
N2 C8 C10 108.15(13) . . ?
C11 C8 C10 110.00(14) . . ?
N2 C8 C9 108.37(13) . . ?
C11 C8 C9 110.33(14) . . ?
C10 C8 C9 110.81(14) . . ?
N2 C1 N1 106.45(13) . . ?
O2 C3 N2 130.17(15) . . ?
O2 C3 C2 125.68(14) . . ?
N2 C3 C2 104.12(13) . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N1 C4 C5 109.22(13) . . ?
N1 C4 C7 108.80(13) . . ?
C5 C4 C7 109.28(15) . . ?
N1 C4 C6 107.91(13) . . ?
C5 C4 C6 110.69(14) . . ?
C7 C4 C6 110.91(15) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C4 C6 H6A 109.5 . . ?
C4 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C4 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.305
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.044
_database_code_depnum_ccdc_archive 'CCDC 983772'
#######################################################################
#
#                 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_5DACNH3_3

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            5DACNH3
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H21 N3 O2'
_chemical_formula_sum            'C11 H21 N3 O2'
_chemical_formula_weight         227.31

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 Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   P21_21_21

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                   9.102(3)
_cell_length_b                   12.188(4)
_cell_length_c                   23.505(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2607.5(16)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       needles
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.158
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             992
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   none

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            34428
_diffrn_reflns_av_R_equivalents  0.0919
_diffrn_reflns_av_sigmaI/netI    0.0481
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.73
_diffrn_reflns_theta_max         24.99
_reflns_number_total             4584
_reflns_number_gt                4349
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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/[σ²(Fo²)+(0.0934P)²+3.4999P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0(3)
_refine_ls_number_reflns         4584
_refine_ls_number_parameters     301
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0897
_refine_ls_R_factor_gt           0.0851
_refine_ls_wR_factor_ref         0.2025
_refine_ls_wR_factor_gt          0.1985
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_restrained_S_all      1.006
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.7309(3) 0.1787(3) 0.05147(12) 0.0400(7) Uani 1 1 d . . .
N1 N 0.8087(4) 0.1100(3) -0.03515(13) 0.0307(8) Uani 1 1 d . . .
C1 C 0.9379(4) 0.0470(3) -0.05574(16) 0.0308(9) Uani 1 1 d . . .
H1A H 0.9043 -0.0140 -0.0796 0.037 Uiso 1 1 calc R . .
O2 O 0.9470(3) 0.0256(2) 0.09438(11) 0.0388(7) Uani 1 1 d . . .
N2 N 0.9986(3) 0.0030(3) -0.00180(13) 0.0321(7) Uani 1 1 d . . .
C2 C 0.8105(4) 0.1211(3) 0.02105(16) 0.0331(9) Uani 1 1 d . . .
C3 C 0.9282(4) 0.0440(3) 0.04370(16) 0.0290(8) Uani 1 1 d . . .
N3 N 1.0335(4) 0.1152(3) -0.08789(14) 0.0390(8) Uani 1 1 d . . .
H3A H 1.1207 0.1287 -0.0757 0.047 Uiso 1 1 calc R . .
H3B H 1.0041 0.1430 -0.1195 0.047 Uiso 1 1 calc R . .
O3 O 0.7102(5) 0.1691(3) 0.36055(13) 0.0587(10) Uani 1 1 d . . .
N4 N 0.8153(4) 0.1377(3) 0.27155(14) 0.0398(9) Uani 1 1 d . . .
O4 O 0.4742(4) 0.0391(3) 0.31301(13) 0.0607(10) Uani 1 1 d . . .
C4 C 0.7025(5) 0.1685(3) -0.07439(18) 0.0373(10) Uani 1 1 d . . .
N5 N 0.6201(4) 0.0438(3) 0.23199(14) 0.0397(9) Uani 1 1 d . . .
C5 C 0.5469(5) 0.1472(4) -0.0526(2) 0.0489(12) Uani 1 1 d . . .
H5A H 0.5264 0.0700 -0.0543 0.073 Uiso 1 1 calc R . .
H5B H 0.4777 0.1861 -0.0759 0.073 Uiso 1 1 calc R . .
H5C H 0.5389 0.1721 -0.0140 0.073 Uiso 1 1 calc R . .
N6 N 0.7452(5) 0.1893(3) 0.17716(15) 0.0484(10) Uani 1 1 d . . .
H6A H 0.7673 0.2548 0.1877 0.058 Uiso 1 1 calc R . .
H6B H 0.7139 0.1776 0.1432 0.058 Uiso 1 1 calc R . .
C6 C 0.7139(5) 0.1193(4) -0.13410(17) 0.0426(11) Uani 1 1 d . . .
H6C H 0.8103 0.1325 -0.1491 0.064 Uiso 1 1 calc R . .
H6D H 0.6419 0.1527 -0.1584 0.064 Uiso 1 1 calc R . .
H6E H 0.6965 0.0417 -0.1322 0.064 Uiso 1 1 calc R . .
C7 C 0.7399(6) 0.2889(4) -0.0743(2) 0.0476(11) Uani 1 1 d . . .
H7A H 0.8387 0.2988 -0.0876 0.071 Uiso 1 1 calc R . .
H7B H 0.7314 0.3172 -0.0364 0.071 Uiso 1 1 calc R . .
H7C H 0.6733 0.3274 -0.0989 0.071 Uiso 1 1 calc R . .
C8 C 1.0963(4) -0.0964(3) -0.00004(17) 0.0333(9) Uani 1 1 d . . .
C9 C 1.2150(6) -0.0799(4) 0.0435(2) 0.0565(14) Uani 1 1 d . . .
H9A H 1.1715 -0.0602 0.0793 0.085 Uiso 1 1 calc R . .
H9B H 1.2797 -0.0224 0.0313 0.085 Uiso 1 1 calc R . .
H9C H 1.2699 -0.1467 0.0479 0.085 Uiso 1 1 calc R . .
C10 C 1.1673(7) -0.1166(6) -0.0578(2) 0.0705(19) Uani 1 1 d . . .
H10A H 1.2212 -0.0525 -0.0692 0.106 Uiso 1 1 calc R . .
H10B H 1.0924 -0.1320 -0.0854 0.106 Uiso 1 1 calc R . .
H10C H 1.2330 -0.1780 -0.0552 0.106 Uiso 1 1 calc R . .
C11 C 0.9995(7) -0.1927(4) 0.0152(3) 0.080(2) Uani 1 1 d . . .
H11A H 0.9639 -0.1841 0.0533 0.121 Uiso 1 1 calc R . .
H11B H 1.0553 -0.2594 0.0124 0.121 Uiso 1 1 calc R . .
H11C H 0.9179 -0.1959 -0.0106 0.121 Uiso 1 1 calc R . .
C12 C 0.7607(5) 0.0990(3) 0.21648(17) 0.0383(10) Uani 1 1 d . . .
H12A H 0.8291 0.0448 0.2008 0.046 Uiso 1 1 calc R . .
C13 C 0.7104(6) 0.1324(4) 0.31171(18) 0.0455(12) Uani 1 1 d . . .
C14 C 0.5847(5) 0.0673(4) 0.28638(18) 0.0431(11) Uani 1 1 d . . .
C15 C 0.9645(6) 0.1875(4) 0.2786(2) 0.0511(12) Uani 1 1 d . . .
C16 C 0.9511(9) 0.3131(4) 0.2798(3) 0.077(2) Uani 1 1 d . . .
H16A H 0.9118 0.3383 0.2442 0.116 Uiso 1 1 calc R . .
H16B H 1.0463 0.3449 0.2857 0.116 Uiso 1 1 calc R . .
H16C H 0.8867 0.3345 0.3101 0.116 Uiso 1 1 calc R . .
C17 C 1.0617(6) 0.1520(4) 0.2289(2) 0.0575(14) Uani 1 1 d . . .
H17A H 1.0623 0.0734 0.2264 0.086 Uiso 1 1 calc R . .
H17B H 1.1600 0.1781 0.2350 0.086 Uiso 1 1 calc R . .
H17C H 1.0238 0.1823 0.1942 0.086 Uiso 1 1 calc R . .
C18 C 1.0316(7) 0.1450(5) 0.3337(2) 0.0689(16) Uani 1 1 d . . .
H18A H 1.0377 0.0664 0.3323 0.103 Uiso 1 1 calc R . .
H18B H 0.9711 0.1666 0.3652 0.103 Uiso 1 1 calc R . .
H18C H 1.1283 0.1752 0.3383 0.103 Uiso 1 1 calc R . .
C19 C 0.5411(5) -0.0344(4) 0.19474(18) 0.0429(11) Uani 1 1 d . . .
C20 C 0.3818(8) 0.0047(12) 0.1890(3) 0.163(6) Uani 1 1 d . . .
H20A H 0.3797 0.0739 0.1695 0.245 Uiso 1 1 calc R . .
H20B H 0.3395 0.0130 0.2262 0.245 Uiso 1 1 calc R . .
H20C H 0.3264 -0.0484 0.1678 0.245 Uiso 1 1 calc R . .
C21 C 0.6053(7) -0.0402(5) 0.1360(2) 0.0669(16) Uani 1 1 d . . .
H21A H 0.7057 -0.0639 0.1383 0.100 Uiso 1 1 calc R . .
H21B H 0.6012 0.0310 0.1186 0.100 Uiso 1 1 calc R . .
H21C H 0.5502 -0.0915 0.1136 0.100 Uiso 1 1 calc R . .
C22 C 0.5469(11) -0.1439(6) 0.2231(3) 0.119(4) Uani 1 1 d . . .
H22A H 0.6469 -0.1689 0.2246 0.178 Uiso 1 1 calc R . .
H22B H 0.4888 -0.1954 0.2019 0.178 Uiso 1 1 calc R . .
H22C H 0.5089 -0.1379 0.2611 0.178 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds 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
O1 C2 1.237(5) . ?
N1 C2 1.328(5) . ?
N1 C1 1.486(5) . ?
N1 C4 1.514(5) . ?
C1 N3 1.421(5) . ?
C1 N2 1.483(5) . ?
C1 H1A 0.9800 . ?
O2 C3 1.224(5) . ?
N2 C3 1.343(5) . ?
N2 C8 1.503(5) . ?
C2 C3 1.521(6) . ?
N3 H3A 0.8600 . ?
N3 H3B 0.8600 . ?
O3 C13 1.232(5) . ?
N4 C13 1.344(6) . ?
N4 C12 1.465(5) . ?
N4 C15 1.497(7) . ?
O4 C14 1.234(6) . ?
C4 C7 1.507(6) . ?
C4 C5 1.528(6) . ?
C4 C6 1.530(6) . ?
N5 C14 1.349(5) . ?
N5 C19 1.481(6) . ?
N5 C12 1.490(6) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
N6 C12 1.445(5) . ?
N6 H6A 0.8600 . ?
N6 H6B 0.8600 . ?
C6 H6C 0.9600 . ?
C6 H6D 0.9600 . ?
C6 H6E 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C9 1.502(6) . ?
C8 C11 1.511(7) . ?
C8 C10 1.523(6) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9800 . ?
C13 C14 1.514(7) . ?
C15 C18 1.523(7) . ?
C15 C17 1.527(7) . ?
C15 C16 1.535(7) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 C22 1.494(8) . ?
C19 C21 1.500(7) . ?
C19 C20 1.531(8) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?

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
C2 N1 C1 111.5(3) . . ?
C2 N1 C4 124.5(3) . . ?
C1 N1 C4 123.4(3) . . ?
N3 C1 N2 116.0(3) . . ?
N3 C1 N1 110.8(3) . . ?
N2 C1 N1 101.7(3) . . ?
N3 C1 H1A 109.3 . . ?
N2 C1 H1A 109.3 . . ?
N1 C1 H1A 109.3 . . ?
C3 N2 C1 111.6(3) . . ?
C3 N2 C8 124.1(3) . . ?
C1 N2 C8 122.4(3) . . ?
O1 C2 N1 128.7(4) . . ?
O1 C2 C3 124.1(3) . . ?
N1 C2 C3 107.1(3) . . ?
O2 C3 N2 129.8(4) . . ?
O2 C3 C2 123.5(3) . . ?
N2 C3 C2 106.7(3) . . ?
C1 N3 H3A 120.0 . . ?
C1 N3 H3B 120.0 . . ?
H3A N3 H3B 120.0 . . ?
C13 N4 C12 111.3(4) . . ?
C13 N4 C15 125.9(4) . . ?
C12 N4 C15 122.4(3) . . ?
C7 C4 N1 108.3(4) . . ?
C7 C4 C5 112.0(4) . . ?
N1 C4 C5 107.9(4) . . ?
C7 C4 C6 111.6(4) . . ?
N1 C4 C6 109.4(3) . . ?
C5 C4 C6 107.6(4) . . ?
C14 N5 C19 125.5(4) . . ?
C14 N5 C12 109.9(4) . . ?
C19 N5 C12 124.2(3) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C12 N6 H6A 120.0 . . ?
C12 N6 H6B 120.0 . . ?
H6A N6 H6B 120.0 . . ?
C4 C6 H6C 109.5 . . ?
C4 C6 H6D 109.5 . . ?
H6C C6 H6D 109.5 . . ?
C4 C6 H6E 109.5 . . ?
H6C C6 H6E 109.5 . . ?
H6D C6 H6E 109.5 . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 N2 109.7(3) . . ?
C9 C8 C11 111.2(5) . . ?
N2 C8 C11 106.7(4) . . ?
C9 C8 C10 108.9(4) . . ?
N2 C8 C10 110.9(3) . . ?
C11 C8 C10 109.4(4) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N6 C12 N4 110.7(3) . . ?
N6 C12 N5 114.6(4) . . ?
N4 C12 N5 102.7(3) . . ?
N6 C12 H12A 109.5 . . ?
N4 C12 H12A 109.5 . . ?
N5 C12 H12A 109.5 . . ?
O3 C13 N4 129.7(5) . . ?
O3 C13 C14 123.8(4) . . ?
N4 C13 C14 106.6(4) . . ?
O4 C14 N5 128.1(5) . . ?
O4 C14 C13 124.2(4) . . ?
N5 C14 C13 107.7(4) . . ?
N4 C15 C18 108.6(4) . . ?
N4 C15 C17 109.0(4) . . ?
C18 C15 C17 108.7(5) . . ?
N4 C15 C16 109.6(5) . . ?
C18 C15 C16 110.8(5) . . ?
C17 C15 C16 110.0(4) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N5 C19 C22 107.1(4) . . ?
N5 C19 C21 112.6(4) . . ?
C22 C19 C21 110.7(6) . . ?
N5 C19 C20 108.2(6) . . ?
C22 C19 C20 110.5(7) . . ?
C21 C19 C20 107.6(5) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.337
_refine_diff_density_min         -0.336
_refine_diff_density_rms         0.051
_database_code_depnum_ccdc_archive 'CCDC 983773'
#######################################################################
#
#                 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_5DACMeVinylKetone_4

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            5DACMeVinylKetone
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H24 N2 O3'
_chemical_formula_sum            'C15 H24 N2 O3'
_chemical_formula_weight         280.36

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 Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   6.1949(2)
_cell_length_b                   13.0960(3)
_cell_length_c                   9.5555(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.800(2)
_cell_angle_gamma                90.00
_cell_volume                     773.52(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.204
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             304
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   none

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            20735
_diffrn_reflns_av_R_equivalents  0.0346
_diffrn_reflns_av_sigmaI/netI    0.0187
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.14
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2727
_reflns_number_gt                2621
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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/[σ²(Fo²)+(0.0529P)²+0.1131P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.4(9)
_refine_ls_number_reflns         2727
_refine_ls_number_parameters     188
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0303
_refine_ls_R_factor_gt           0.0285
_refine_ls_wR_factor_ref         0.0798
_refine_ls_wR_factor_gt          0.0781
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_restrained_S_all      1.006
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
N1 N 0.21847(19) 0.79409(9) 0.01094(12) 0.0225(3) Uani 1 1 d . . .
O1 O 0.24169(19) 0.94519(9) -0.11334(12) 0.0380(3) Uani 1 1 d . . .
C1 C 0.3109(2) 0.75559(11) 0.14688(15) 0.0207(3) Uani 1 1 d . . .
O2 O 0.47860(19) 1.01212(9) 0.13957(15) 0.0418(3) Uani 1 1 d . . .
N2 N 0.4094(2) 0.84760(10) 0.21195(13) 0.0249(3) Uani 1 1 d . . .
C2 C 0.2779(2) 0.89153(11) -0.01026(17) 0.0273(3) Uani 1 1 d . . .
O3 O 0.14173(15) 0.71976(7) 0.22858(10) 0.0222(2) Uani 1 1 d . . .
C3 C 0.4028(2) 0.92667(12) 0.12227(18) 0.0289(3) Uani 1 1 d . . .
C4 C 0.0760(2) 0.73771(12) -0.09762(15) 0.0263(3) Uani 1 1 d . . .
C5 C 0.1928(3) 0.73407(16) -0.23394(16) 0.0399(4) Uani 1 1 d . . .
H5A H 0.2289 0.8022 -0.2612 0.060 Uiso 1 1 calc R . .
H5B H 0.0999 0.7033 -0.3065 0.060 Uiso 1 1 calc R . .
H5C H 0.3227 0.6944 -0.2195 0.060 Uiso 1 1 calc R . .
C6 C 0.0253(3) 0.62908(12) -0.05519(17) 0.0302(4) Uani 1 1 d . . .
H6A H -0.0499 0.6301 0.0295 0.045 Uiso 1 1 calc R . .
H6B H 0.1576 0.5914 -0.0396 0.045 Uiso 1 1 calc R . .
H6C H -0.0640 0.5971 -0.1286 0.045 Uiso 1 1 calc R . .
C7 C -0.1357(3) 0.79738(15) -0.1165(2) 0.0400(4) Uani 1 1 d . . .
H7A H -0.2013 0.8012 -0.0284 0.060 Uiso 1 1 calc R . .
H7B H -0.2322 0.7633 -0.1840 0.060 Uiso 1 1 calc R . .
H7C H -0.1067 0.8651 -0.1489 0.060 Uiso 1 1 calc R . .
C8 C 0.5157(3) 0.85832(13) 0.35810(16) 0.0327(4) Uani 1 1 d . . .
C9 C 0.7544(3) 0.88383(15) 0.3452(2) 0.0408(4) Uani 1 1 d . . .
H9A H 0.8220 0.8297 0.2964 0.061 Uiso 1 1 calc R . .
H9B H 0.8250 0.8914 0.4371 0.061 Uiso 1 1 calc R . .
H9C H 0.7660 0.9464 0.2940 0.061 Uiso 1 1 calc R . .
C10 C 0.4987(3) 0.76259(15) 0.44575(18) 0.0444(5) Uani 1 1 d . . .
H10A H 0.5656 0.7066 0.4003 0.067 Uiso 1 1 calc R . .
H10B H 0.3491 0.7471 0.4559 0.067 Uiso 1 1 calc R . .
H10C H 0.5706 0.7734 0.5367 0.067 Uiso 1 1 calc R . .
C11 C 0.3995(3) 0.94485(18) 0.4303(2) 0.0517(5) Uani 1 1 d . . .
H11A H 0.4177 1.0075 0.3802 0.078 Uiso 1 1 calc R . .
H11B H 0.4598 0.9522 0.5250 0.078 Uiso 1 1 calc R . .
H11C H 0.2482 0.9292 0.4311 0.078 Uiso 1 1 calc R . .
C12 C 0.4682(2) 0.66456(11) 0.13468(15) 0.0233(3) Uani 1 1 d . . .
H12A H 0.4779 0.6442 0.0377 0.028 Uiso 1 1 calc R . .
H12B H 0.6117 0.6811 0.1751 0.028 Uiso 1 1 calc R . .
C13 C 0.3649(3) 0.58317(11) 0.21698(16) 0.0273(3) Uani 1 1 d . . .
H13A H 0.4191 0.5175 0.2313 0.033 Uiso 1 1 calc R . .
C14 C 0.1861(2) 0.61813(11) 0.26619(15) 0.0248(3) Uani 1 1 d . . .
C15 C 0.0228(3) 0.57261(13) 0.35359(16) 0.0327(4) Uani 1 1 d . . .
H15A H 0.0614 0.5031 0.3751 0.049 Uiso 1 1 calc R . .
H15B H -0.1165 0.5744 0.3033 0.049 Uiso 1 1 calc R . .
H15C H 0.0176 0.6108 0.4391 0.049 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds 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
N1 C2 1.3471(18) . ?
N1 C1 1.4735(18) . ?
N1 C4 1.5094(19) . ?
O1 C2 1.2186(19) . ?
C1 O3 1.4272(17) . ?
C1 N2 1.4697(19) . ?
C1 C12 1.5488(19) . ?
O2 C3 1.2206(19) . ?
N2 C3 1.343(2) . ?
N2 C8 1.511(2) . ?
C2 C3 1.511(2) . ?
O3 C14 1.4012(17) . ?
C4 C6 1.518(2) . ?
C4 C7 1.527(2) . ?
C4 C5 1.532(2) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C10 1.515(3) . ?
C8 C9 1.529(2) . ?
C8 C11 1.531(2) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C13 1.493(2) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.314(2) . ?
C13 H13A 0.9300 . ?
C14 C15 1.479(2) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?

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
C2 N1 C1 111.25(12) . . ?
C2 N1 C4 120.87(13) . . ?
C1 N1 C4 127.87(11) . . ?
O3 C1 N2 109.71(11) . . ?
O3 C1 N1 109.76(10) . . ?
N2 C1 N1 102.63(11) . . ?
O3 C1 C12 106.05(11) . . ?
N2 C1 C12 114.68(11) . . ?
N1 C1 C12 114.00(11) . . ?
C3 N2 C1 111.59(12) . . ?
C3 N2 C8 120.74(13) . . ?
C1 N2 C8 127.63(12) . . ?
O1 C2 N1 129.06(16) . . ?
O1 C2 C3 123.94(14) . . ?
N1 C2 C3 106.99(13) . . ?
C14 O3 C1 108.29(10) . . ?
O2 C3 N2 128.70(16) . . ?
O2 C3 C2 124.31(15) . . ?
N2 C3 C2 106.99(13) . . ?
N1 C4 C6 113.38(12) . . ?
N1 C4 C7 106.81(13) . . ?
C6 C4 C7 108.63(12) . . ?
N1 C4 C5 108.20(12) . . ?
C6 C4 C5 108.41(14) . . ?
C7 C4 C5 111.46(14) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C4 C6 H6A 109.5 . . ?
C4 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C4 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N2 C8 C10 113.08(13) . . ?
N2 C8 C9 108.10(13) . . ?
C10 C8 C9 109.18(15) . . ?
N2 C8 C11 107.22(14) . . ?
C10 C8 C11 108.13(15) . . ?
C9 C8 C11 111.15(15) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 C1 102.49(11) . . ?
C13 C12 H12A 111.3 . . ?
C1 C12 H12A 111.3 . . ?
C13 C12 H12B 111.3 . . ?
C1 C12 H12B 111.3 . . ?
H12A C12 H12B 109.2 . . ?
C14 C13 C12 109.91(13) . . ?
C14 C13 H13A 125.0 . . ?
C12 C13 H13A 125.0 . . ?
C13 C14 O3 113.27(12) . . ?
C13 C14 C15 133.31(15) . . ?
O3 C14 C15 113.43(13) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.070
_database_code_depnum_ccdc_archive 'CCDC 983774'
#######################################################################
#
#                 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_5DACPhButyne_5

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            5DACPhButyne
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H28 N2 O2'
_chemical_formula_sum            'C21 H28 N2 O2'
_chemical_formula_weight         340.45

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 Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.1753(6)
_cell_length_b                   22.7039(14)
_cell_length_c                   18.5417(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.125(5)
_cell_angle_gamma                90.00
_cell_volume                     3832.7(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.180
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1472
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   none

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            144570
_diffrn_reflns_av_R_equivalents  0.2417
_diffrn_reflns_av_sigmaI/netI    0.0967
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.42
_diffrn_reflns_theta_max         25.00
_reflns_number_total             6729
_reflns_number_gt                3571
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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/[σ²(Fo²)+(0.0545P)²+4.0091P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6729
_refine_ls_number_parameters     465
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1462
_refine_ls_R_factor_gt           0.0594
_refine_ls_wR_factor_ref         0.1648
_refine_ls_wR_factor_gt          0.1175
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_restrained_S_all      1.006
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
N1 N 0.5205(3) 0.88343(11) 0.23381(14) 0.0241(7) Uani 1 1 d . . .
O1 O 0.6310(3) 0.84305(11) 0.13909(14) 0.0392(7) Uani 1 1 d . . .
C1 C 0.5737(3) 0.91651(14) 0.30065(17) 0.0223(8) Uani 1 1 d . . .
O2 O 0.8859(3) 0.90108(11) 0.20977(14) 0.0400(7) Uani 1 1 d . . .
N2 N 0.7276(3) 0.93033(11) 0.29094(14) 0.0238(7) Uani 1 1 d . . .
C2 C 0.6314(4) 0.87289(15) 0.19445(19) 0.0266(8) Uani 1 1 d . . .
O3 O 0.3961(3) 0.61010(10) 0.21005(13) 0.0357(6) Uani 1 1 d . . .
N3 N 0.2868(3) 0.63676(12) 0.31116(14) 0.0251(7) Uani 1 1 d . . .
C3 C 0.7657(4) 0.90319(15) 0.23134(19) 0.0281(8) Uani 1 1 d . . .
O4 O 0.1258(3) 0.65154(10) 0.13336(13) 0.0397(7) Uani 1 1 d . . .
N4 N 0.0753(3) 0.67688(12) 0.24881(14) 0.0253(7) Uani 1 1 d . . .
C4 C 0.3721(4) 0.85493(15) 0.21550(19) 0.0280(8) Uani 1 1 d . . .
C5 C 0.2546(4) 0.88253(19) 0.2557(2) 0.0515(12) Uani 1 1 d . . .
H5A H 0.2742 0.8733 0.3065 0.077 Uiso 1 1 calc R . .
H5B H 0.1601 0.8672 0.2366 0.077 Uiso 1 1 calc R . .
H5C H 0.2553 0.9245 0.2493 0.077 Uiso 1 1 calc R . .
C6 C 0.3891(4) 0.79000(16) 0.2350(2) 0.0480(11) Uani 1 1 d . . .
H6A H 0.4179 0.7861 0.2863 0.072 Uiso 1 1 calc R . .
H6B H 0.4630 0.7728 0.2091 0.072 Uiso 1 1 calc R . .
H6C H 0.2973 0.7702 0.2218 0.072 Uiso 1 1 calc R . .
C7 C 0.3224(4) 0.86284(18) 0.1343(2) 0.0466(11) Uani 1 1 d . . .
H7A H 0.3327 0.9034 0.1213 0.070 Uiso 1 1 calc R . .
H7B H 0.2214 0.8513 0.1237 0.070 Uiso 1 1 calc R . .
H7C H 0.3819 0.8388 0.1070 0.070 Uiso 1 1 calc R . .
C8 C 0.8413(4) 0.95968(15) 0.34503(19) 0.0289(8) Uani 1 1 d . . .
C9 C 0.9397(4) 0.91100(17) 0.3820(2) 0.0446(11) Uani 1 1 d . . .
H9A H 0.9829 0.8890 0.3458 0.067 Uiso 1 1 calc R . .
H9B H 0.8818 0.8851 0.4079 0.067 Uiso 1 1 calc R . .
H9C H 1.0160 0.9284 0.4154 0.067 Uiso 1 1 calc R . .
C10 C 0.9299(4) 1.00190(15) 0.3036(2) 0.0359(9) Uani 1 1 d . . .
H10A H 0.9890 0.9798 0.2740 0.054 Uiso 1 1 calc R . .
H10B H 0.9923 1.0255 0.3375 0.054 Uiso 1 1 calc R . .
H10C H 0.8641 1.0270 0.2732 0.054 Uiso 1 1 calc R . .
C11 C 0.7747(4) 0.99524(17) 0.4021(2) 0.0425(10) Uani 1 1 d . . .
H11A H 0.7267 0.9691 0.4324 0.064 Uiso 1 1 calc R . .
H11B H 0.7044 1.0226 0.3786 0.064 Uiso 1 1 calc R . .
H11C H 0.8509 1.0165 0.4314 0.064 Uiso 1 1 calc R . .
C12 C 0.3221(4) 1.01530(16) 0.41011(19) 0.0347(9) Uani 1 1 d . . .
H12A H 0.2712 1.0523 0.4094 0.052 Uiso 1 1 calc R . .
H12B H 0.3952 1.0137 0.4518 0.052 Uiso 1 1 calc R . .
H12C H 0.2534 0.9837 0.4125 0.052 Uiso 1 1 calc R . .
C13 C 0.3954(4) 1.00930(15) 0.3416(2) 0.0326(9) Uani 1 1 d . . .
H13A H 0.3209 1.0106 0.2997 0.039 Uiso 1 1 calc R . .
H13B H 0.4611 1.0424 0.3383 0.039 Uiso 1 1 calc R . .
C14 C 0.4797(3) 0.95370(14) 0.34008(18) 0.0241(8) Uani 1 1 d . . .
C15 C 0.5249(3) 0.90400(14) 0.37169(18) 0.0241(8) Uani 1 1 d . . .
C16 C 0.5335(4) 0.86164(14) 0.43116(18) 0.0243(8) Uani 1 1 d . . .
C17 C 0.4574(4) 0.87091(15) 0.49053(18) 0.0294(8) Uani 1 1 d . . .
H17A H 0.3995 0.9044 0.4925 0.035 Uiso 1 1 calc R . .
C18 C 0.4678(4) 0.83033(17) 0.54685(19) 0.0372(10) Uani 1 1 d . . .
H18A H 0.4169 0.8365 0.5865 0.045 Uiso 1 1 calc R . .
C19 C 0.5539(4) 0.78085(17) 0.5438(2) 0.0389(10) Uani 1 1 d . . .
H19A H 0.5615 0.7538 0.5818 0.047 Uiso 1 1 calc R . .
C20 C 0.6286(4) 0.77115(16) 0.4850(2) 0.0377(10) Uani 1 1 d . . .
H20A H 0.6855 0.7374 0.4832 0.045 Uiso 1 1 calc R . .
C21 C 0.6192(4) 0.81134(15) 0.42884(19) 0.0307(9) Uani 1 1 d . . .
H21A H 0.6703 0.8048 0.3893 0.037 Uiso 1 1 calc R . .
C22 C 0.1489(3) 0.66749(15) 0.32324(18) 0.0269(8) Uani 1 1 d . . .
C23 C 0.2962(4) 0.63109(14) 0.23945(19) 0.0264(8) Uani 1 1 d . . .
C24 C 0.1559(4) 0.65426(14) 0.1991(2) 0.0264(8) Uani 1 1 d . . .
C25 C 0.4059(4) 0.61303(15) 0.36680(19) 0.0299(8) Uani 1 1 d . . .
C26 C 0.5496(4) 0.64278(17) 0.3541(2) 0.0405(10) Uani 1 1 d . . .
H26A H 0.5404 0.6846 0.3595 0.061 Uiso 1 1 calc R . .
H26B H 0.5712 0.6340 0.3059 0.061 Uiso 1 1 calc R . .
H26C H 0.6277 0.6285 0.3890 0.061 Uiso 1 1 calc R . .
C27 C 0.3806(4) 0.62495(19) 0.44490(19) 0.0433(10) Uani 1 1 d . . .
H27A H 0.2909 0.6064 0.4544 0.065 Uiso 1 1 calc R . .
H27B H 0.3738 0.6666 0.4524 0.065 Uiso 1 1 calc R . .
H27C H 0.4610 0.6093 0.4773 0.065 Uiso 1 1 calc R . .
C28 C 0.4143(4) 0.54651(16) 0.3555(2) 0.0421(10) Uani 1 1 d . . .
H28A H 0.3211 0.5290 0.3612 0.063 Uiso 1 1 calc R . .
H28B H 0.4888 0.5301 0.3907 0.063 Uiso 1 1 calc R . .
H28C H 0.4381 0.5386 0.3075 0.063 Uiso 1 1 calc R . .
C29 C -0.0751(4) 0.70230(15) 0.22658(19) 0.0308(9) Uani 1 1 d . . .
C30 C -0.1738(4) 0.65216(17) 0.1961(2) 0.0458(11) Uani 1 1 d . . .
H30A H -0.1363 0.6359 0.1543 0.069 Uiso 1 1 calc R . .
H30B H -0.2714 0.6668 0.1822 0.069 Uiso 1 1 calc R . .
H30C H -0.1759 0.6222 0.2324 0.069 Uiso 1 1 calc R . .
C31 C -0.1433(4) 0.73159(18) 0.2881(2) 0.0464(11) Uani 1 1 d . . .
H31A H -0.0796 0.7623 0.3090 0.070 Uiso 1 1 calc R . .
H31B H -0.1567 0.7029 0.3247 0.070 Uiso 1 1 calc R . .
H31C H -0.2367 0.7481 0.2695 0.070 Uiso 1 1 calc R . .
C32 C -0.0625(4) 0.74939(17) 0.1689(2) 0.0449(11) Uani 1 1 d . . .
H32A H 0.0019 0.7801 0.1891 0.067 Uiso 1 1 calc R . .
H32B H -0.1579 0.7656 0.1534 0.067 Uiso 1 1 calc R . .
H32C H -0.0237 0.7321 0.1281 0.067 Uiso 1 1 calc R . .
C33 C 0.1062(4) 0.78036(18) 0.4825(2) 0.0457(11) Uani 1 1 d . . .
H33A H 0.1307 0.8198 0.4981 0.068 Uiso 1 1 calc R . .
H33B H 0.1416 0.7532 0.5203 0.068 Uiso 1 1 calc R . .
H33C H 0.0015 0.7767 0.4719 0.068 Uiso 1 1 calc R . .
C34 C 0.1769(4) 0.76669(16) 0.41480(19) 0.0355(9) Uani 1 1 d . . .
H34A H 0.1473 0.7964 0.3783 0.043 Uiso 1 1 calc R . .
H34B H 0.2828 0.7690 0.4265 0.043 Uiso 1 1 calc R . .
C35 C 0.1379(4) 0.70806(15) 0.38403(18) 0.0287(8) Uani 1 1 d . . .
C36 C 0.0714(3) 0.65699(15) 0.38633(18) 0.0254(8) Uani 1 1 d . . .
C37 C -0.0174(4) 0.61527(16) 0.42072(19) 0.0322(9) Uani 1 1 d . . .
C38 C -0.0702(4) 0.62847(18) 0.4863(2) 0.0412(10) Uani 1 1 d . . .
H38A H -0.0474 0.6643 0.5094 0.049 Uiso 1 1 calc R . .
C39 C -0.1574(4) 0.5875(2) 0.5168(2) 0.0546(12) Uani 1 1 d . . .
H39A H -0.1939 0.5959 0.5603 0.065 Uiso 1 1 calc R . .
C40 C -0.1896(5) 0.5344(2) 0.4825(3) 0.0613(14) Uani 1 1 d . . .
H40A H -0.2481 0.5071 0.5030 0.074 Uiso 1 1 calc R . .
C41 C -0.1362(5) 0.52136(19) 0.4184(3) 0.0533(12) Uani 1 1 d . . .
H41A H -0.1580 0.4853 0.3958 0.064 Uiso 1 1 calc R . .
C42 C -0.0512(4) 0.56116(17) 0.3875(2) 0.0421(10) Uani 1 1 d . . .
H42A H -0.0156 0.5521 0.3441 0.050 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds 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
N1 C2 1.345(4) . ?
N1 C1 1.479(4) . ?
N1 C4 1.507(4) . ?
O1 C2 1.230(4) . ?
C1 C14 1.465(4) . ?
C1 C15 1.470(4) . ?
C1 N2 1.480(4) . ?
O2 C3 1.220(4) . ?
N2 C3 1.349(4) . ?
N2 C8 1.510(4) . ?
C2 C3 1.500(5) . ?
O3 C23 1.220(4) . ?
N3 C23 1.349(4) . ?
N3 C22 1.486(4) . ?
N3 C25 1.506(4) . ?
O4 C24 1.218(4) . ?
N4 C24 1.352(4) . ?
N4 C22 1.475(4) . ?
N4 C29 1.505(4) . ?
C4 C5 1.520(5) . ?
C4 C6 1.521(5) . ?
C4 C7 1.528(5) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C11 1.519(5) . ?
C8 C10 1.524(5) . ?
C8 C9 1.534(5) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C13 1.515(5) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.483(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.315(4) . ?
C15 C16 1.458(4) . ?
C16 C17 1.391(5) . ?
C16 C21 1.390(5) . ?
C17 C18 1.387(5) . ?
C17 H17A 0.9300 . ?
C18 C19 1.378(5) . ?
C18 H18A 0.9300 . ?
C19 C20 1.375(5) . ?
C19 H19A 0.9300 . ?
C20 C21 1.380(5) . ?
C20 H20A 0.9300 . ?
C21 H21A 0.9300 . ?
C22 C36 1.461(5) . ?
C22 C35 1.469(5) . ?
C23 C24 1.502(5) . ?
C25 C27 1.519(5) . ?
C25 C26 1.525(5) . ?
C25 C28 1.528(5) . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C29 C30 1.519(5) . ?
C29 C31 1.520(5) . ?
C29 C32 1.526(5) . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
C33 C34 1.514(5) . ?
C33 H33A 0.9600 . ?
C33 H33B 0.9600 . ?
C33 H33C 0.9600 . ?
C34 C35 1.475(5) . ?
C34 H34A 0.9700 . ?
C34 H34B 0.9700 . ?
C35 C36 1.313(5) . ?
C36 C37 1.448(5) . ?
C37 C42 1.391(5) . ?
C37 C38 1.397(5) . ?
C38 C39 1.392(6) . ?
C38 H38A 0.9300 . ?
C39 C40 1.378(6) . ?
C39 H39A 0.9300 . ?
C40 C41 1.374(6) . ?
C40 H40A 0.9300 . ?
C41 C42 1.365(5) . ?
C41 H41A 0.9300 . ?
C42 H42A 0.9300 . ?

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
C2 N1 C1 110.6(3) . . ?
C2 N1 C4 121.6(3) . . ?
C1 N1 C4 127.0(3) . . ?
C14 C1 C15 53.2(2) . . ?
C14 C1 N1 123.9(3) . . ?
C15 C1 N1 123.2(3) . . ?
C14 C1 N2 124.6(3) . . ?
C15 C1 N2 123.4(3) . . ?
N1 C1 N2 103.1(2) . . ?
C3 N2 C1 110.5(3) . . ?
C3 N2 C8 121.2(3) . . ?
C1 N2 C8 127.2(3) . . ?
O1 C2 N1 128.8(3) . . ?
O1 C2 C3 123.4(3) . . ?
N1 C2 C3 107.7(3) . . ?
C23 N3 C22 110.7(3) . . ?
C23 N3 C25 120.7(3) . . ?
C22 N3 C25 128.6(3) . . ?
O2 C3 N2 128.5(3) . . ?
O2 C3 C2 123.9(3) . . ?
N2 C3 C2 107.6(3) . . ?
C24 N4 C22 110.9(3) . . ?
C24 N4 C29 121.3(3) . . ?
C22 N4 C29 127.5(3) . . ?
N1 C4 C5 112.8(3) . . ?
N1 C4 C6 107.4(3) . . ?
C5 C4 C6 109.9(3) . . ?
N1 C4 C7 108.8(3) . . ?
C5 C4 C7 106.9(3) . . ?
C6 C4 C7 110.9(3) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C4 C6 H6A 109.5 . . ?
C4 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C4 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N2 C8 C11 113.1(3) . . ?
N2 C8 C10 108.1(3) . . ?
C11 C8 C10 107.6(3) . . ?
N2 C8 C9 107.4(3) . . ?
C11 C8 C9 109.7(3) . . ?
C10 C8 C9 110.9(3) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 H12A 109.5 . . ?
C13 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C13 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 C12 112.3(3) . . ?
C14 C13 H13A 109.1 . . ?
C12 C13 H13A 109.1 . . ?
C14 C13 H13B 109.1 . . ?
C12 C13 H13B 109.1 . . ?
H13A C13 H13B 107.9 . . ?
C15 C14 C1 63.6(2) . . ?
C15 C14 C13 149.1(3) . . ?
C1 C14 C13 147.2(3) . . ?
C14 C15 C16 152.6(3) . . ?
C14 C15 C1 63.2(2) . . ?
C16 C15 C1 144.2(3) . . ?
C17 C16 C21 119.4(3) . . ?
C17 C16 C15 120.9(3) . . ?
C21 C16 C15 119.7(3) . . ?
C18 C17 C16 120.1(3) . . ?
C18 C17 H17A 120.0 . . ?
C16 C17 H17A 120.0 . . ?
C19 C18 C17 119.8(4) . . ?
C19 C18 H18A 120.1 . . ?
C17 C18 H18A 120.1 . . ?
C20 C19 C18 120.5(3) . . ?
C20 C19 H19A 119.8 . . ?
C18 C19 H19A 119.8 . . ?
C19 C20 C21 120.1(4) . . ?
C19 C20 H20A 119.9 . . ?
C21 C20 H20A 119.9 . . ?
C20 C21 C16 120.2(3) . . ?
C20 C21 H21A 119.9 . . ?
C16 C21 H21A 119.9 . . ?
C36 C22 C35 53.3(2) . . ?
C36 C22 N4 124.1(3) . . ?
C35 C22 N4 124.1(3) . . ?
C36 C22 N3 123.5(3) . . ?
C35 C22 N3 123.4(3) . . ?
N4 C22 N3 103.1(2) . . ?
O3 C23 N3 128.4(3) . . ?
O3 C23 C24 124.0(3) . . ?
N3 C23 C24 107.6(3) . . ?
O4 C24 N4 128.8(3) . . ?
O4 C24 C23 123.7(3) . . ?
N4 C24 C23 107.5(3) . . ?
N3 C25 C27 113.9(3) . . ?
N3 C25 C26 107.7(3) . . ?
C27 C25 C26 107.8(3) . . ?
N3 C25 C28 107.7(3) . . ?
C27 C25 C28 108.9(3) . . ?
C26 C25 C28 111.0(3) . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C25 C27 H27A 109.5 . . ?
C25 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C25 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C25 C28 H28A 109.5 . . ?
C25 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C25 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
N4 C29 C30 107.4(3) . . ?
N4 C29 C31 114.3(3) . . ?
C30 C29 C31 109.0(3) . . ?
N4 C29 C32 108.3(3) . . ?
C30 C29 C32 110.9(3) . . ?
C31 C29 C32 107.0(3) . . ?
C29 C30 H30A 109.5 . . ?
C29 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C29 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C29 C31 H31A 109.5 . . ?
C29 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C29 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C29 C32 H32A 109.5 . . ?
C29 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C29 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C34 C33 H33A 109.5 . . ?
C34 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C34 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C35 C34 C33 113.4(3) . . ?
C35 C34 H34A 108.9 . . ?
C33 C34 H34A 108.9 . . ?
C35 C34 H34B 108.9 . . ?
C33 C34 H34B 108.9 . . ?
H34A C34 H34B 107.7 . . ?
C36 C35 C22 63.1(2) . . ?
C36 C35 C34 151.1(3) . . ?
C22 C35 C34 145.7(3) . . ?
C35 C36 C37 151.7(3) . . ?
C35 C36 C22 63.6(2) . . ?
C37 C36 C22 144.6(3) . . ?
C42 C37 C38 119.5(3) . . ?
C42 C37 C36 119.3(3) . . ?
C38 C37 C36 121.2(3) . . ?
C39 C38 C37 119.3(4) . . ?
C39 C38 H38A 120.3 . . ?
C37 C38 H38A 120.3 . . ?
C40 C39 C38 119.9(4) . . ?
C40 C39 H39A 120.1 . . ?
C38 C39 H39A 120.1 . . ?
C41 C40 C39 120.6(4) . . ?
C41 C40 H40A 119.7 . . ?
C39 C40 H40A 119.7 . . ?
C42 C41 C40 120.3(4) . . ?
C42 C41 H41A 119.9 . . ?
C40 C41 H41A 119.9 . . ?
C41 C42 C37 120.5(4) . . ?
C41 C42 H42A 119.8 . . ?
C37 C42 H42A 119.8 . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.224
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.052
_database_code_depnum_ccdc_archive 'CCDC 983775'
#######################################################################
#
#                 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_5DACToluene_7

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            5DACToluene
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C18 H26 N2 O2); C6 H6'
_chemical_formula_sum            'C42 H58 N4 O4'
_chemical_formula_weight         682.92

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 Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   17.9469(10)
_cell_length_b                   17.5630(8)
_cell_length_c                   12.2414(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.152(2)
_cell_angle_gamma                90.00
_cell_volume                     3858.5(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.23
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.176
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1480
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   none

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            18906
_diffrn_reflns_av_R_equivalents  0.0313
_diffrn_reflns_av_sigmaI/netI    0.0368
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.13
_diffrn_reflns_theta_max         25.00
_reflns_number_total             6694
_reflns_number_gt                5245
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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/[σ²(Fo²)+(0.0480P)²+1.5762P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6694
_refine_ls_number_parameters     463
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0590
_refine_ls_R_factor_gt           0.0422
_refine_ls_wR_factor_ref         0.1113
_refine_ls_wR_factor_gt          0.0986
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_restrained_S_all      1.006
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
N1 N 0.16696(7) 1.26336(7) 0.30283(10) 0.0230(3) Uani 1 1 d . . .
O1 O 0.17968(8) 1.31665(7) 0.13114(10) 0.0427(3) Uani 1 1 d . . .
C1 C 0.20689(9) 1.20503(8) 0.36660(12) 0.0198(3) Uani 1 1 d . . .
H1A H 0.2234 1.2271 0.4380 0.024 Uiso 1 1 calc R . .
N2 N 0.27230(7) 1.18875(7) 0.29850(10) 0.0225(3) Uani 1 1 d . . .
O2 O 0.30960(8) 1.22221(8) 0.12317(10) 0.0491(4) Uani 1 1 d . . .
C2 C 0.19770(10) 1.27274(9) 0.20404(13) 0.0274(4) Uani 1 1 d . . .
O3 O 0.39559(7) 0.78789(7) 0.58257(9) 0.0350(3) Uani 1 1 d . . .
N3 N 0.35639(7) 0.81327(7) 0.40540(10) 0.0217(3) Uani 1 1 d . . .
C3 C 0.26689(10) 1.22340(9) 0.20055(13) 0.0293(4) Uani 1 1 d . . .
O4 O 0.26592(7) 0.69061(7) 0.58160(9) 0.0324(3) Uani 1 1 d . . .
N4 N 0.24961(7) 0.74112(7) 0.40833(10) 0.0200(3) Uani 1 1 d . . .
C4 C 0.10971(9) 1.31717(9) 0.34769(14) 0.0285(4) Uani 1 1 d . . .
C5 C 0.04161(12) 1.31602(15) 0.2734(3) 0.0788(9) Uani 1 1 d . . .
H5A H 0.0560 1.3322 0.1998 0.118 Uiso 1 1 calc R . .
H5B H 0.0038 1.3508 0.3021 0.118 Uiso 1 1 calc R . .
H5C H 0.0213 1.2643 0.2704 0.118 Uiso 1 1 calc R . .
C6 C 0.08777(17) 1.29673(14) 0.4622(2) 0.0820(10) Uani 1 1 d . . .
H6A H 0.1325 1.2925 0.5078 0.123 Uiso 1 1 calc R . .
H6B H 0.0613 1.2479 0.4619 0.123 Uiso 1 1 calc R . .
H6C H 0.0551 1.3364 0.4918 0.123 Uiso 1 1 calc R . .
C7 C 0.14410(13) 1.39611(10) 0.34933(18) 0.0479(5) Uani 1 1 d . . .
H7A H 0.1879 1.3961 0.3974 0.072 Uiso 1 1 calc R . .
H7B H 0.1075 1.4329 0.3765 0.072 Uiso 1 1 calc R . .
H7C H 0.1591 1.4103 0.2752 0.072 Uiso 1 1 calc R . .
C8 C 0.34560(9) 1.16130(9) 0.34472(14) 0.0283(4) Uani 1 1 d . . .
C9 C 0.39254(10) 1.23168(11) 0.36919(16) 0.0376(4) Uani 1 1 d . . .
H9A H 0.3697 1.2605 0.4290 0.056 Uiso 1 1 calc R . .
H9B H 0.3951 1.2638 0.3038 0.056 Uiso 1 1 calc R . .
H9C H 0.4429 1.2160 0.3905 0.056 Uiso 1 1 calc R . .
C10 C 0.38467(11) 1.11025(12) 0.26169(18) 0.0456(5) Uani 1 1 d . . .
H10A H 0.3961 1.1398 0.1959 0.068 Uiso 1 1 calc R . .
H10B H 0.3520 1.0676 0.2424 0.068 Uiso 1 1 calc R . .
H10C H 0.4310 1.0906 0.2935 0.068 Uiso 1 1 calc R . .
C11 C 0.33351(10) 1.11706(10) 0.45013(15) 0.0357(4) Uani 1 1 d . . .
H11A H 0.3053 1.1485 0.5017 0.054 Uiso 1 1 calc R . .
H11B H 0.3819 1.1038 0.4823 0.054 Uiso 1 1 calc R . .
H11C H 0.3056 1.0704 0.4343 0.054 Uiso 1 1 calc R . .
C12 C 0.15897(9) 1.13350(9) 0.38710(12) 0.0224(3) Uani 1 1 d . . .
H12A H 0.1888 1.0971 0.4308 0.027 Uiso 1 1 calc R . .
H12B H 0.1156 1.1486 0.4320 0.027 Uiso 1 1 calc R . .
C13 C 0.13038(9) 1.09236(8) 0.28698(12) 0.0219(3) Uani 1 1 d . . .
C14 C 0.17713(10) 1.04867(9) 0.22201(14) 0.0288(4) Uani 1 1 d . . .
H14A H 0.2292 1.0487 0.2365 0.035 Uiso 1 1 calc R . .
C15 C 0.14984(11) 1.00512(10) 0.13687(14) 0.0350(4) Uani 1 1 d . . .
H15A H 0.1831 0.9759 0.0935 0.042 Uiso 1 1 calc R . .
C16 C 0.07445(11) 1.00397(10) 0.11461(15) 0.0353(4) Uani 1 1 d . . .
H16A H 0.0554 0.9735 0.0569 0.042 Uiso 1 1 calc R . .
C17 C 0.02720(11) 1.04758(10) 0.17721(15) 0.0351(4) Uani 1 1 d . . .
H17A H -0.0247 1.0477 0.1619 0.042 Uiso 1 1 calc R . .
C18 C 0.05486(9) 1.09137(9) 0.26240(14) 0.0282(4) Uani 1 1 d . . .
H18A H 0.0215 1.1212 0.3047 0.034 Uiso 1 1 calc R . .
C19 C 0.28910(8) 0.79692(8) 0.34012(12) 0.0192(3) Uani 1 1 d . . .
H19A H 0.3036 0.7729 0.2692 0.023 Uiso 1 1 calc R . .
C20 C 0.28316(9) 0.73270(9) 0.50604(12) 0.0230(4) Uani 1 1 d . . .
C21 C 0.35220(9) 0.78216(9) 0.50547(12) 0.0236(4) Uani 1 1 d . . .
C22 C 0.18645(9) 0.69081(9) 0.37203(13) 0.0238(4) Uani 1 1 d . . .
C23 C 0.12249(10) 0.69803(10) 0.45387(16) 0.0358(4) Uani 1 1 d . . .
H23A H 0.1384 0.6780 0.5249 0.054 Uiso 1 1 calc R . .
H23B H 0.0794 0.6689 0.4275 0.054 Uiso 1 1 calc R . .
H23C H 0.1086 0.7517 0.4615 0.054 Uiso 1 1 calc R . .
C24 C 0.15911(10) 0.71282(10) 0.25856(14) 0.0328(4) Uani 1 1 d . . .
H24A H 0.2014 0.7145 0.2082 0.049 Uiso 1 1 calc R . .
H24B H 0.1354 0.7631 0.2616 0.049 Uiso 1 1 calc R . .
H24C H 0.1229 0.6751 0.2329 0.049 Uiso 1 1 calc R . .
C25 C 0.21582(10) 0.60923(9) 0.36873(15) 0.0314(4) Uani 1 1 d . . .
H25A H 0.2552 0.6053 0.3137 0.047 Uiso 1 1 calc R . .
H25B H 0.1751 0.5745 0.3498 0.047 Uiso 1 1 calc R . .
H25C H 0.2360 0.5955 0.4405 0.047 Uiso 1 1 calc R . .
C26 C 0.42674(9) 0.84872(9) 0.36197(13) 0.0259(4) Uani 1 1 d . . .
C27 C 0.48743(11) 0.78795(11) 0.36820(18) 0.0437(5) Uani 1 1 d . . .
H27A H 0.4900 0.7676 0.4427 0.066 Uiso 1 1 calc R . .
H27B H 0.5355 0.8106 0.3488 0.066 Uiso 1 1 calc R . .
H27C H 0.4757 0.7467 0.3171 0.066 Uiso 1 1 calc R . .
C28 C 0.41886(11) 0.87388(12) 0.24327(15) 0.0404(5) Uani 1 1 d . . .
H28A H 0.3830 0.9159 0.2386 0.061 Uiso 1 1 calc R . .
H28B H 0.4011 0.8310 0.1990 0.061 Uiso 1 1 calc R . .
H28C H 0.4674 0.8909 0.2160 0.061 Uiso 1 1 calc R . .
C29 C 0.44705(10) 0.91730(10) 0.43240(15) 0.0352(4) Uani 1 1 d . . .
H29A H 0.4069 0.9550 0.4288 0.053 Uiso 1 1 calc R . .
H29B H 0.4933 0.9401 0.4054 0.053 Uiso 1 1 calc R . .
H29C H 0.4540 0.9009 0.5083 0.053 Uiso 1 1 calc R . .
C30 C 0.24312(9) 0.86973(9) 0.31811(12) 0.0227(3) Uani 1 1 d . . .
H30A H 0.2777 0.9099 0.2927 0.027 Uiso 1 1 calc R . .
H30B H 0.2081 0.8590 0.2574 0.027 Uiso 1 1 calc R . .
C31 C 0.19889(9) 0.90120(8) 0.41236(12) 0.0214(3) Uani 1 1 d . . .
C32 C 0.23266(9) 0.93229(9) 0.50469(13) 0.0243(4) Uani 1 1 d . . .
H32A H 0.2854 0.9310 0.5113 0.029 Uiso 1 1 calc R . .
C33 C 0.19078(10) 0.96499(9) 0.58703(14) 0.0295(4) Uani 1 1 d . . .
H33A H 0.2150 0.9867 0.6488 0.035 Uiso 1 1 calc R . .
C34 C 0.11388(10) 0.96625(9) 0.57981(14) 0.0313(4) Uani 1 1 d . . .
H34A H 0.0850 0.9885 0.6364 0.038 Uiso 1 1 calc R . .
C35 C 0.07952(10) 0.93484(10) 0.48956(15) 0.0328(4) Uani 1 1 d . . .
H35A H 0.0267 0.9348 0.4844 0.039 Uiso 1 1 calc R . .
C36 C 0.12147(10) 0.90334(9) 0.40656(14) 0.0285(4) Uani 1 1 d . . .
H36A H 0.0970 0.8828 0.3443 0.034 Uiso 1 1 calc R . .
C37 C 0.41057(12) 0.56667(15) 0.2851(2) 0.0605(7) Uani 1 1 d . . .
H37A H 0.4258 0.6085 0.2414 0.073 Uiso 1 1 calc R . .
C38 C 0.42108(14) 0.56847(15) 0.3961(2) 0.0655(7) Uani 1 1 d . . .
H38A H 0.4437 0.6116 0.4293 0.079 Uiso 1 1 calc R . .
C39 C 0.39886(15) 0.50805(14) 0.4592(2) 0.0639(7) Uani 1 1 d . . .
H39A H 0.4064 0.5092 0.5360 0.077 Uiso 1 1 calc R . .
C40 C 0.36583(14) 0.44595(13) 0.4114(2) 0.0602(6) Uani 1 1 d . . .
H40A H 0.3499 0.4044 0.4552 0.072 Uiso 1 1 calc R . .
C41 C 0.35576(13) 0.44394(14) 0.3004(2) 0.0593(6) Uani 1 1 d . . .
H41A H 0.3333 0.4008 0.2671 0.071 Uiso 1 1 calc R . .
C42 C 0.37818(12) 0.50446(15) 0.2376(2) 0.0563(6) Uani 1 1 d . . .
H42A H 0.3711 0.5031 0.1607 0.068 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds 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
N1 C2 1.341(2) . ?
N1 C1 1.4729(19) . ?
N1 C4 1.501(2) . ?
O1 C2 1.222(2) . ?
C1 N2 1.470(2) . ?
C1 C12 1.543(2) . ?
C1 H1A 1.0000 . ?
N2 C3 1.348(2) . ?
N2 C8 1.510(2) . ?
O2 C3 1.220(2) . ?
C2 C3 1.515(2) . ?
O3 C21 1.2261(19) . ?
N3 C21 1.344(2) . ?
N3 C19 1.4746(19) . ?
N3 C26 1.506(2) . ?
O4 C20 1.2243(19) . ?
N4 C20 1.3458(19) . ?
N4 C19 1.4707(19) . ?
N4 C22 1.503(2) . ?
C4 C6 1.501(3) . ?
C4 C7 1.518(3) . ?
C4 C5 1.522(3) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C11 1.522(2) . ?
C8 C9 1.525(2) . ?
C8 C10 1.527(2) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.511(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C18 1.388(2) . ?
C13 C14 1.389(2) . ?
C14 C15 1.381(2) . ?
C14 H14A 0.9500 . ?
C15 C16 1.380(3) . ?
C15 H15A 0.9500 . ?
C16 C17 1.377(3) . ?
C16 H16A 0.9500 . ?
C17 C18 1.387(2) . ?
C17 H17A 0.9500 . ?
C18 H18A 0.9500 . ?
C19 C30 1.545(2) . ?
C19 H19A 1.0000 . ?
C20 C21 1.513(2) . ?
C22 C24 1.522(2) . ?
C22 C25 1.527(2) . ?
C22 C23 1.531(2) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 C29 1.525(2) . ?
C26 C28 1.525(2) . ?
C26 C27 1.527(2) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C30 C31 1.507(2) . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C31 C36 1.392(2) . ?
C31 C32 1.393(2) . ?
C32 C33 1.384(2) . ?
C32 H32A 0.9500 . ?
C33 C34 1.383(3) . ?
C33 H33A 0.9500 . ?
C34 C35 1.379(3) . ?
C34 H34A 0.9500 . ?
C35 C36 1.382(2) . ?
C35 H35A 0.9500 . ?
C36 H36A 0.9500 . ?
C37 C42 1.367(3) . ?
C37 C38 1.372(3) . ?
C37 H37A 0.9500 . ?
C38 C39 1.372(3) . ?
C38 H38A 0.9500 . ?
C39 C40 1.371(3) . ?
C39 H39A 0.9500 . ?
C40 C41 1.371(3) . ?
C40 H40A 0.9500 . ?
C41 C42 1.373(3) . ?
C41 H41A 0.9500 . ?
C42 H42A 0.9500 . ?

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
C2 N1 C1 111.27(13) . . ?
C2 N1 C4 122.43(13) . . ?
C1 N1 C4 125.21(13) . . ?
N2 C1 N1 102.88(11) . . ?
N2 C1 C12 112.34(12) . . ?
N1 C1 C12 112.44(13) . . ?
N2 C1 H1A 109.7 . . ?
N1 C1 H1A 109.7 . . ?
C12 C1 H1A 109.7 . . ?
C3 N2 C1 111.16(13) . . ?
C3 N2 C8 122.57(14) . . ?
C1 N2 C8 123.10(12) . . ?
O1 C2 N1 128.85(16) . . ?
O1 C2 C3 123.75(16) . . ?
N1 C2 C3 107.12(13) . . ?
C21 N3 C19 111.53(13) . . ?
C21 N3 C26 122.62(13) . . ?
C19 N3 C26 125.13(12) . . ?
O2 C3 N2 129.70(17) . . ?
O2 C3 C2 123.25(15) . . ?
N2 C3 C2 106.88(14) . . ?
C20 N4 C19 111.27(12) . . ?
C20 N4 C22 122.23(13) . . ?
C19 N4 C22 126.01(12) . . ?
C6 C4 N1 111.88(14) . . ?
C6 C4 C7 108.29(18) . . ?
N1 C4 C7 107.54(14) . . ?
C6 C4 C5 110.1(2) . . ?
N1 C4 C5 108.80(15) . . ?
C7 C4 C5 110.25(18) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C4 C6 H6A 109.5 . . ?
C4 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C4 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N2 C8 C11 110.77(14) . . ?
N2 C8 C9 107.16(13) . . ?
C11 C8 C9 109.10(15) . . ?
N2 C8 C10 109.83(14) . . ?
C11 C8 C10 109.34(15) . . ?
C9 C8 C10 110.62(15) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 C1 116.45(13) . . ?
C13 C12 H12A 108.2 . . ?
C1 C12 H12A 108.2 . . ?
C13 C12 H12B 108.2 . . ?
C1 C12 H12B 108.2 . . ?
H12A C12 H12B 107.3 . . ?
C18 C13 C14 117.40(15) . . ?
C18 C13 C12 120.74(15) . . ?
C14 C13 C12 121.62(14) . . ?
C15 C14 C13 121.62(16) . . ?
C15 C14 H14A 119.2 . . ?
C13 C14 H14A 119.2 . . ?
C16 C15 C14 120.18(17) . . ?
C16 C15 H15A 119.9 . . ?
C14 C15 H15A 119.9 . . ?
C17 C16 C15 119.14(16) . . ?
C17 C16 H16A 120.4 . . ?
C15 C16 H16A 120.4 . . ?
C16 C17 C18 120.48(17) . . ?
C16 C17 H17A 119.8 . . ?
C18 C17 H17A 119.8 . . ?
C17 C18 C13 121.17(17) . . ?
C17 C18 H18A 119.4 . . ?
C13 C18 H18A 119.4 . . ?
N4 C19 N3 102.55(11) . . ?
N4 C19 C30 113.12(12) . . ?
N3 C19 C30 111.69(12) . . ?
N4 C19 H19A 109.8 . . ?
N3 C19 H19A 109.8 . . ?
C30 C19 H19A 109.8 . . ?
O4 C20 N4 128.64(15) . . ?
O4 C20 C21 123.95(14) . . ?
N4 C20 C21 107.29(13) . . ?
O3 C21 N3 129.16(16) . . ?
O3 C21 C20 124.19(14) . . ?
N3 C21 C20 106.59(13) . . ?
N4 C22 C24 111.19(13) . . ?
N4 C22 C25 107.41(13) . . ?
C24 C22 C25 108.94(14) . . ?
N4 C22 C23 108.91(13) . . ?
C24 C22 C23 109.61(14) . . ?
C25 C22 C23 110.76(14) . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C22 C24 H24A 109.5 . . ?
C22 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C22 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C22 C25 H25A 109.5 . . ?
C22 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C22 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
N3 C26 C29 109.04(13) . . ?
N3 C26 C28 112.36(13) . . ?
C29 C26 C28 109.35(15) . . ?
N3 C26 C27 106.98(14) . . ?
C29 C26 C27 110.76(15) . . ?
C28 C26 C27 108.33(15) . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C26 C28 H28A 109.5 . . ?
C26 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C26 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C26 C29 H29A 109.5 . . ?
C26 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C26 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C31 C30 C19 116.87(12) . . ?
C31 C30 H30A 108.1 . . ?
C19 C30 H30A 108.1 . . ?
C31 C30 H30B 108.1 . . ?
C19 C30 H30B 108.1 . . ?
H30A C30 H30B 107.3 . . ?
C36 C31 C32 117.58(15) . . ?
C36 C31 C30 119.92(14) . . ?
C32 C31 C30 122.42(14) . . ?
C33 C32 C31 121.20(16) . . ?
C33 C32 H32A 119.4 . . ?
C31 C32 H32A 119.4 . . ?
C34 C33 C32 120.26(16) . . ?
C34 C33 H33A 119.9 . . ?
C32 C33 H33A 119.9 . . ?
C35 C34 C33 119.27(16) . . ?
C35 C34 H34A 120.4 . . ?
C33 C34 H34A 120.4 . . ?
C34 C35 C36 120.39(17) . . ?
C34 C35 H35A 119.8 . . ?
C36 C35 H35A 119.8 . . ?
C35 C36 C31 121.29(16) . . ?
C35 C36 H36A 119.4 . . ?
C31 C36 H36A 119.4 . . ?
C42 C37 C38 119.8(2) . . ?
C42 C37 H37A 120.1 . . ?
C38 C37 H37A 120.1 . . ?
C37 C38 C39 120.0(2) . . ?
C37 C38 H38A 120.0 . . ?
C39 C38 H38A 120.0 . . ?
C40 C39 C38 120.1(2) . . ?
C40 C39 H39A 120.0 . . ?
C38 C39 H39A 120.0 . . ?
C41 C40 C39 119.9(2) . . ?
C41 C40 H40A 120.0 . . ?
C39 C40 H40A 120.0 . . ?
C40 C41 C42 119.8(2) . . ?
C40 C41 H41A 120.1 . . ?
C42 C41 H41A 120.1 . . ?
C37 C42 C41 120.3(2) . . ?
C37 C42 H42A 119.8 . . ?
C41 C42 H42A 119.8 . . ?

_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.985
_refine_diff_density_max         0.263
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.037
_database_code_depnum_ccdc_archive 'CCDC 983776'
