# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2015

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

data_Faouzi3
_database_code_depnum_ccdc_archive 'CCDC 1020806'
_audit_update_record             
;
2014-08-22 deposited with the CCDC.
2015-01-30 downloaded from the CCDC.
;
#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C15 H11 N O2'
_chemical_formula_sum            'C15 H11 N O2'
_chemical_formula_weight         237.25
_chemical_compound_source        'synthesis as described'

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

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.1432(4)
_cell_length_b                   8.4932(4)
_cell_length_c                   10.1874(5)
_cell_angle_alpha                99.388(2)
_cell_angle_beta                 97.577(2)
_cell_angle_gamma                106.771(2)
_cell_volume                     573.27(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    193(2)
_cell_measurement_reflns_used    5043
_cell_measurement_theta_min      2.56
_cell_measurement_theta_max      30.77
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             248
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker-AXS)'
_exptl_absorpt_correction_T_min  0.9909
_exptl_absorpt_correction_T_max  0.9927

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

_diffrn_ambient_temperature      193(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'microfocus sealed tube'
_diffrn_radiation_monochromator  'multilayer optics'
_diffrn_measurement_device_type  'Bruker Kappa APEX II Quazar'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_radiation_probe          x-ray
_diffrn_reflns_av_R_equivalents  0.0205
_diffrn_reflns_av_unetI/netI     0.0173
_diffrn_reflns_number            8247
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.38
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_full        25.35
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_reflns_number_total             2080
_reflns_number_gt                1880
_reflns_threshold_expression     >2sigma(I)

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

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

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

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

_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)+(0.0461P)²+0.1280P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.069(7)
_refine_ls_number_reflns         2080
_refine_ls_number_parameters     164
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0375
_refine_ls_R_factor_gt           0.034
_refine_ls_wR_factor_ref         0.0899
_refine_ls_wR_factor_gt          0.0871
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.019
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.23
_refine_diff_density_min         -0.19
_refine_diff_density_rms         0.055

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

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.13209(16) 0.43414(15) 0.75453(12) 0.0302(3) Uani 1 1 d . . .
C2 C 0.18231(16) 0.37930(15) 0.88234(12) 0.0297(3) Uani 1 1 d . . .
C3 C 0.17832(18) 0.22277(16) 0.90453(14) 0.0375(3) Uani 1 1 d . . .
H3 H 0.1374 0.1271 0.8319 0.045 Uiso 1 1 calc R . .
C4 C 0.23636(19) 0.20979(17) 1.03713(15) 0.0426(3) Uani 1 1 d . . .
H4 H 0.236 0.1036 1.0556 0.051 Uiso 1 1 calc R . .
C5 C 0.29484(18) 0.34992(18) 1.14286(14) 0.0411(3) Uani 1 1 d . . .
H5 H 0.3329 0.3377 1.2326 0.049 Uiso 1 1 calc R . .
C6 C 0.29880(18) 0.50752(17) 1.12009(12) 0.0357(3) Uani 1 1 d . . .
H6 H 0.3389 0.6033 1.1925 0.043 Uiso 1 1 calc R . .
C7 C 0.24230(16) 0.51960(15) 0.98815(12) 0.0294(3) Uani 1 1 d . . .
C8 C 0.23248(16) 0.66764(15) 0.93021(12) 0.0300(3) Uani 1 1 d . . .
C9 C 0.14779(18) 0.71410(15) 0.69420(13) 0.0340(3) Uani 1 1 d . . .
H9A H 0.1065 0.8086 0.7373 0.041 Uiso 1 1 calc R . .
H9B H 0.043 0.6479 0.6148 0.041 Uiso 1 1 calc R . .
C10 C 0.34135(17) 0.78327(15) 0.64747(12) 0.0310(3) Uani 1 1 d . . .
C11 C 0.38781(19) 0.69085(17) 0.53826(12) 0.0384(3) Uani 1 1 d . . .
H11 H 0.2946 0.5863 0.4902 0.046 Uiso 1 1 calc R . .
C12 C 0.5685(2) 0.7499(2) 0.49906(14) 0.0464(4) Uani 1 1 d . . .
H12 H 0.6001 0.6853 0.425 0.056 Uiso 1 1 calc R . .
C13 C 0.7040(2) 0.9035(2) 0.56787(15) 0.0491(4) Uani 1 1 d . . .
H13 H 0.828 0.9447 0.5405 0.059 Uiso 1 1 calc R . .
C14 C 0.6585(2) 0.99607(17) 0.67585(15) 0.0453(4) Uani 1 1 d . . .
H14 H 0.7511 1.1014 0.7229 0.054 Uiso 1 1 calc R . .
C15 C 0.47831(19) 0.93619(16) 0.71617(13) 0.0378(3) Uani 1 1 d . . .
H15 H 0.4482 1.0002 0.7913 0.045 Uiso 1 1 calc R . .
N1 N 0.16669(14) 0.60671(12) 0.79107(9) 0.0296(2) Uani 1 1 d . . .
O1 O 0.07203(14) 0.35011(11) 0.64047(9) 0.0418(3) Uani 1 1 d . . .
O2 O 0.27098(14) 0.81263(11) 0.98719(9) 0.0419(3) Uani 1 1 d . . .



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

_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
C1 O1 1.2104(15) . ?
C1 N1 1.3916(16) . ?
C1 C2 1.4872(17) . ?
C2 C3 1.3775(17) . ?
C2 C7 1.3892(17) . ?
C3 C4 1.3914(19) . ?
C3 H3 0.95 . ?
C4 C5 1.388(2) . ?
C4 H4 0.95 . ?
C5 C6 1.3883(19) . ?
C5 H5 0.95 . ?
C6 C7 1.3806(17) . ?
C6 H6 0.95 . ?
C7 C8 1.4887(17) . ?
C8 O2 1.2076(14) . ?
C8 N1 1.3937(15) . ?
C9 N1 1.4675(15) . ?
C9 C10 1.5099(16) . ?
C9 H9A 0.99 . ?
C9 H9B 0.99 . ?
C10 C15 1.3869(17) . ?
C10 C11 1.3880(18) . ?
C11 C12 1.3803(19) . ?
C11 H11 0.95 . ?
C12 C13 1.387(2) . ?
C12 H12 0.95 . ?
C13 C14 1.376(2) . ?
C13 H13 0.95 . ?
C14 C15 1.3835(19) . ?
C14 H14 0.95 . ?
C15 H15 0.95 . ?

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
O1 C1 N1 125.26(11) . . ?
O1 C1 C2 128.73(11) . . ?
N1 C1 C2 106.01(10) . . ?
C3 C2 C7 121.41(11) . . ?
C3 C2 C1 130.52(11) . . ?
C7 C2 C1 108.07(10) . . ?
C2 C3 C4 117.60(12) . . ?
C2 C3 H3 121.2 . . ?
C4 C3 H3 121.2 . . ?
C5 C4 C3 120.89(12) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C6 C5 C4 121.34(12) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C7 C6 C5 117.43(12) . . ?
C7 C6 H6 121.3 . . ?
C5 C6 H6 121.3 . . ?
C6 C7 C2 121.32(11) . . ?
C6 C7 C8 130.72(11) . . ?
C2 C7 C8 107.95(10) . . ?
O2 C8 N1 124.78(11) . . ?
O2 C8 C7 129.27(11) . . ?
N1 C8 C7 105.95(9) . . ?
N1 C9 C10 111.58(9) . . ?
N1 C9 H9A 109.3 . . ?
C10 C9 H9A 109.3 . . ?
N1 C9 H9B 109.3 . . ?
C10 C9 H9B 109.3 . . ?
H9A C9 H9B 108 . . ?
C15 C10 C11 119.16(12) . . ?
C15 C10 C9 120.60(11) . . ?
C11 C10 C9 120.18(11) . . ?
C12 C11 C10 120.43(12) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C11 C12 C13 119.99(13) . . ?
C11 C12 H12 120 . . ?
C13 C12 H12 120 . . ?
C14 C13 C12 119.86(13) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C13 C14 C15 120.20(13) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C14 C15 C10 120.35(13) . . ?
C14 C15 H15 119.8 . . ?
C10 C15 H15 119.8 . . ?
C1 N1 C8 112.02(10) . . ?
C1 N1 C9 124.19(10) . . ?
C8 N1 C9 123.71(10) . . ?
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_Faouzi10
_database_code_depnum_ccdc_archive 'CCDC 1020807'
_audit_update_record             
;
2014-08-22 deposited with the CCDC.
2015-01-30 downloaded from the CCDC.
;

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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C22 H20 N2 O4'
_chemical_formula_sum            'C22 H20 N2 O4'
_chemical_formula_weight         376.4
_chemical_compound_source        'synthesis as described'

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14
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                   7.0179(8)
_cell_length_b                   4.6365(4)
_cell_length_c                   29.074(3)
_cell_angle_alpha                90
_cell_angle_beta                 92.757(3)
_cell_angle_gamma                90
_cell_volume                     944.93(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    193(2)
_cell_measurement_reflns_used    2882
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      24.07
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.04
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             396
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker-AXS)'
_exptl_absorpt_correction_T_min  0.9836
_exptl_absorpt_correction_T_max  0.9963

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

_diffrn_ambient_temperature      193(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'microfocus sealed tube'
_diffrn_radiation_monochromator  'multilayer optics'
_diffrn_measurement_device_type  'Bruker Kappa APEX II Quazar'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_radiation_probe          x-ray
_diffrn_reflns_av_R_equivalents  0.0402
_diffrn_reflns_av_unetI/netI     0.043
_diffrn_reflns_number            7457
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_theta_min         4.45
_diffrn_reflns_theta_max         26.6
_diffrn_reflns_theta_full        26.6
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_reflns_number_total             1947
_reflns_number_gt                1364
_reflns_threshold_expression     >2sigma(I)

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

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

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

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

_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)+(0.0412P)²+0.1847P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         1947
_refine_ls_number_parameters     127
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0705
_refine_ls_R_factor_gt           0.0445
_refine_ls_wR_factor_ref         0.1093
_refine_ls_wR_factor_gt          0.0972
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.159
_refine_diff_density_min         -0.17
_refine_diff_density_rms         0.041

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

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2064(2) 0.2904(4) 0.15427(5) 0.0326(4) Uani 1 1 d . . .
C2 C 0.0661(2) 0.4952(3) 0.17261(5) 0.0300(4) Uani 1 1 d . . .
C3 C 0.0732(2) 0.6554(4) 0.21261(6) 0.0361(4) Uani 1 1 d . . .
H3 H 0.1801 0.646 0.2339 0.043 Uiso 1 1 calc R . .
C4 C -0.0822(3) 0.8312(4) 0.22059(6) 0.0416(5) Uani 1 1 d . . .
H4 H -0.0819 0.9433 0.2479 0.05 Uiso 1 1 calc R . .
C5 C -0.2369(3) 0.8460(4) 0.18951(6) 0.0455(5) Uani 1 1 d . . .
H5 H -0.3405 0.9699 0.1957 0.055 Uiso 1 1 calc R . .
C6 C -0.2436(2) 0.6827(4) 0.14937(6) 0.0447(5) Uani 1 1 d . . .
H6 H -0.3504 0.6916 0.1281 0.054 Uiso 1 1 calc R . .
C7 C -0.0896(2) 0.5071(4) 0.14155(5) 0.0339(4) Uani 1 1 d . . .
C8 C -0.0535(3) 0.3090(4) 0.10286(6) 0.0410(4) Uani 1 1 d . . .
C9 C 0.2201(3) -0.0150(4) 0.08286(6) 0.0407(4) Uani 1 1 d . . .
H9A H 0.1222 -0.1351 0.0664 0.049 Uiso 1 1 calc R . .
H9B H 0.3036 -0.1449 0.1018 0.049 Uiso 1 1 calc R . .
C10 C 0.3385(3) 0.1367(4) 0.04796(6) 0.0387(4) Uani 1 1 d . . .
H10A H 0.4303 0.2674 0.0643 0.046 Uiso 1 1 calc R . .
H10B H 0.2536 0.2557 0.0275 0.046 Uiso 1 1 calc R . .
C11 C 0.4470(2) -0.0741(4) 0.01896(5) 0.0351(4) Uani 1 1 d . . .
H11A H 0.3562 -0.2157 0.0049 0.042 Uiso 1 1 calc R . .
H11B H 0.5399 -0.1812 0.0392 0.042 Uiso 1 1 calc R . .
N1 N 0.12566(19) 0.1862(3) 0.11308(4) 0.0353(4) Uani 1 1 d . . .
O1 O 0.36143(17) 0.2209(3) 0.17088(4) 0.0471(4) Uani 1 1 d . . .
O2 O -0.15238(19) 0.2559(3) 0.06875(5) 0.0653(4) Uani 1 1 d . . .



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

_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
C1 O1 1.2126(19) . ?
C1 N1 1.387(2) . ?
C1 C2 1.485(2) . ?
C2 C3 1.379(2) . ?
C2 C7 1.385(2) . ?
C3 C4 1.390(2) . ?
C3 H3 0.95 . ?
C4 C5 1.380(3) . ?
C4 H4 0.95 . ?
C5 C6 1.390(3) . ?
C5 H5 0.95 . ?
C6 C7 1.381(2) . ?
C6 H6 0.95 . ?
C7 C8 1.484(2) . ?
C8 O2 1.208(2) . ?
C8 N1 1.399(2) . ?
C9 N1 1.462(2) . ?
C9 C10 1.515(2) . ?
C9 H9A 0.99 . ?
C9 H9B 0.99 . ?
C10 C11 1.519(2) . ?
C10 H10A 0.99 . ?
C10 H10B 0.99 . ?
C11 C11 1.523(3) 3_655 ?
C11 H11A 0.99 . ?
C11 H11B 0.99 . ?

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
O1 C1 N1 124.94(16) . . ?
O1 C1 C2 128.65(15) . . ?
N1 C1 C2 106.41(13) . . ?
C3 C2 C7 121.58(15) . . ?
C3 C2 C1 130.51(15) . . ?
C7 C2 C1 107.91(14) . . ?
C2 C3 C4 117.37(16) . . ?
C2 C3 H3 121.3 . . ?
C4 C3 H3 121.3 . . ?
C5 C4 C3 121.24(17) . . ?
C5 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?
C4 C5 C6 121.09(17) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C7 C6 C5 117.66(17) . . ?
C7 C6 H6 121.2 . . ?
C5 C6 H6 121.2 . . ?
C6 C7 C2 121.05(16) . . ?
C6 C7 C8 130.83(16) . . ?
C2 C7 C8 108.12(14) . . ?
O2 C8 N1 124.49(17) . . ?
O2 C8 C7 129.50(17) . . ?
N1 C8 C7 106.01(14) . . ?
N1 C9 C10 112.68(14) . . ?
N1 C9 H9A 109.1 . . ?
C10 C9 H9A 109.1 . . ?
N1 C9 H9B 109.1 . . ?
C10 C9 H9B 109.1 . . ?
H9A C9 H9B 107.8 . . ?
C9 C10 C11 112.28(14) . . ?
C9 C10 H10A 109.1 . . ?
C11 C10 H10A 109.1 . . ?
C9 C10 H10B 109.1 . . ?
C11 C10 H10B 109.1 . . ?
H10A C10 H10B 107.9 . . ?
C10 C11 C11 112.76(17) . 3_655 ?
C10 C11 H11A 109 . . ?
C11 C11 H11A 109 3_655 . ?
C10 C11 H11B 109 . . ?
C11 C11 H11B 109 3_655 . ?
H11A C11 H11B 107.8 . . ?
C1 N1 C8 111.54(14) . . ?
C1 N1 C9 124.28(14) . . ?
C8 N1 C9 124.10(14) . . ?
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_Faouzi11
_database_code_depnum_ccdc_archive 'CCDC 1020808'
_audit_update_record             
;
2014-08-22 deposited with the CCDC.
2015-01-30 downloaded from the CCDC.
;

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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C21 H21 N3 O'
_chemical_formula_sum            'C21 H21 N3 O'
_chemical_formula_weight         331.41
_chemical_compound_source        'synthesis as described'
_chemical_absolute_configuration unk

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P c'
_symmetry_space_group_name_Hall  'P -2yc'
_symmetry_Int_Tables_number      7
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, z+1/2'

_cell_length_a                   18.2723(16)
_cell_length_b                   5.5654(4)
_cell_length_c                   8.7266(7)
_cell_angle_alpha                90
_cell_angle_beta                 103.633(4)
_cell_angle_gamma                90
_cell_volume                     862.43(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    193(2)
_cell_measurement_reflns_used    4440
_cell_measurement_theta_min      3.44
_cell_measurement_theta_max      31.99
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.2
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             352
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.08
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2008)'
_exptl_absorpt_correction_T_min  0.9810
_exptl_absorpt_correction_T_max  0.9841

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

_diffrn_ambient_temperature      193(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'microfocus sealed tube'
_diffrn_radiation_monochromator  'multilayer optics'
_diffrn_measurement_device_type  'Bruker Kappa APEX II Quazar'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_radiation_probe          x-ray
_diffrn_reflns_av_R_equivalents  0.0256
_diffrn_reflns_av_unetI/netI     0.0284
_diffrn_reflns_number            11512
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.67
_diffrn_reflns_theta_max         32.55
_diffrn_reflns_theta_full        32.55
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_reflns_number_total             3137
_reflns_number_gt                2705
_reflns_threshold_expression     >2sigma(I)

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

_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_cell_refinement       'APEX2 and SAINT (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

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

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

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

_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)+(0.0735P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3137
_refine_ls_number_parameters     226
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0506
_refine_ls_R_factor_gt           0.0412
_refine_ls_wR_factor_ref         0.1114
_refine_ls_wR_factor_gt          0.1059
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.312
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.038

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

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.49174(10) -0.0753(3) 0.1670(2) 0.0367(4) Uani 1 1 d . . .
H1 H 0.4665 0.0689 0.1824 0.044 Uiso 1 1 calc R . .
C2 C 0.45784(11) -0.2404(3) 0.0528(2) 0.0399(4) Uani 1 1 d . . .
H2 H 0.4091 -0.2076 -0.0109 0.048 Uiso 1 1 calc R . .
C3 C 0.49415(11) -0.4541(3) 0.0299(2) 0.0380(4) Uani 1 1 d . . .
H3 H 0.47 -0.5626 -0.0501 0.046 Uiso 1 1 calc R . .
C4 C 0.56491(10) -0.5102(3) 0.12218(19) 0.0328(3) Uani 1 1 d . . .
H4 H 0.5897 -0.656 0.1085 0.039 Uiso 1 1 calc R . .
C5 C 0.59763(9) -0.3430(2) 0.23521(18) 0.0268(3) Uani 1 1 d . . .
C6 C 0.56350(9) -0.1257(2) 0.25856(19) 0.0279(3) Uani 1 1 d . . .
C7 C 0.61754(10) -0.0021(3) 0.38015(18) 0.0299(3) Uani 1 1 d . . .
H7 H 0.6117 0.1523 0.4222 0.036 Uiso 1 1 calc R . .
C8 C 0.67799(9) -0.1478(2) 0.42276(18) 0.0270(3) Uani 1 1 d . . .
C9 C 0.75010(10) -0.1305(3) 0.54479(19) 0.0305(3) Uani 1 1 d . . .
H9A H 0.7898 -0.2163 0.5066 0.037 Uiso 1 1 calc R . .
H9B H 0.7441 -0.2121 0.6418 0.037 Uiso 1 1 calc R . .
C10 C 0.77573(10) 0.1282(3) 0.58542(19) 0.0298(3) Uani 1 1 d . . .
H10A H 0.7833 0.2093 0.4894 0.036 Uiso 1 1 calc R . .
H10B H 0.7358 0.2158 0.6218 0.036 Uiso 1 1 calc R . .
C11 C 0.84859(10) 0.1386(3) 0.71316(19) 0.0288(3) Uani 1 1 d . . .
H11A H 0.8895 0.0636 0.673 0.035 Uiso 1 1 calc R . .
H11B H 0.8424 0.0445 0.8056 0.035 Uiso 1 1 calc R . .
C12 C 0.87091(9) 0.3953(3) 0.76494(19) 0.0288(3) Uani 1 1 d . . .
H12A H 0.8816 0.4844 0.6745 0.035 Uiso 1 1 calc R . .
H12B H 0.8278 0.4747 0.7947 0.035 Uiso 1 1 calc R . .
C13 C 0.93819(9) 0.4109(3) 0.90060(17) 0.0264(3) Uani 1 1 d . . .
C14 C 0.97901(9) 0.2318(3) 0.98975(18) 0.0288(3) Uani 1 1 d . . .
H14 H 0.972 0.0632 0.9766 0.035 Uiso 1 1 calc R . .
C15 C 1.09031(11) 0.2424(4) 1.2259(2) 0.0434(4) Uani 1 1 d . . .
H15A H 1.0773 0.0735 1.2432 0.052 Uiso 1 1 calc R . .
H15B H 1.0928 0.3318 1.325 0.052 Uiso 1 1 calc R . .
C16 C 1.16605(10) 0.2502(3) 1.18697(19) 0.0333(3) Uani 1 1 d . . .
C17 C 1.21516(13) 0.4407(4) 1.2379(3) 0.0491(5) Uani 1 1 d . . .
H17 H 1.2013 0.5662 1.2992 0.059 Uiso 1 1 calc R . .
C18 C 1.28453(15) 0.4468(4) 1.1987(4) 0.0634(7) Uani 1 1 d . . .
H18 H 1.318 0.5768 1.2337 0.076 Uiso 1 1 calc R . .
C19 C 1.30511(14) 0.2676(5) 1.1104(3) 0.0636(7) Uani 1 1 d . . .
H19 H 1.3526 0.2741 1.0839 0.076 Uiso 1 1 calc R . .
C20 C 1.25711(16) 0.0771(5) 1.0595(3) 0.0596(6) Uani 1 1 d . . .
H20 H 1.2715 -0.0478 0.9983 0.072 Uiso 1 1 calc R . .
C21 C 1.18813(13) 0.0694(4) 1.0982(2) 0.0450(4) Uani 1 1 d . . .
H21 H 1.1552 -0.062 1.0635 0.054 Uiso 1 1 calc R . .
N1 N 0.96763(9) 0.6254(2) 0.96041(17) 0.0334(3) Uani 1 1 d . . .
N2 N 1.02445(10) 0.5860(3) 1.08226(18) 0.0373(3) Uani 1 1 d . . .
N3 N 1.03104(9) 0.3469(2) 1.09984(17) 0.0325(3) Uani 1 1 d . . .
O1 O 0.66730(7) -0.36018(18) 0.33669(13) 0.0288(2) Uani 1 1 d . . .



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

_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
C1 C2 1.390(3) . ?
C1 C6 1.394(2) . ?
C1 H1 0.95 . ?
C2 C3 1.398(3) . ?
C2 H2 0.95 . ?
C3 C4 1.388(3) . ?
C3 H3 0.95 . ?
C4 C5 1.385(2) . ?
C4 H4 0.95 . ?
C5 O1 1.372(2) . ?
C5 C6 1.3976(19) . ?
C6 C7 1.442(2) . ?
C7 C8 1.350(2) . ?
C7 H7 0.95 . ?
C8 O1 1.3893(17) . ?
C8 C9 1.489(2) . ?
C9 C10 1.529(2) . ?
C9 H9A 0.99 . ?
C9 H9B 0.99 . ?
C10 C11 1.523(2) . ?
C10 H10A 0.99 . ?
C10 H10B 0.99 . ?
C11 C12 1.525(2) . ?
C11 H11A 0.99 . ?
C11 H11B 0.99 . ?
C12 C13 1.495(2) . ?
C12 H12A 0.99 . ?
C12 H12B 0.99 . ?
C13 N1 1.362(2) . ?
C13 C14 1.372(2) . ?
C14 N3 1.344(2) . ?
C14 H14 0.95 . ?
C15 N3 1.470(2) . ?
C15 C16 1.501(3) . ?
C15 H15A 0.99 . ?
C15 H15B 0.99 . ?
C16 C21 1.386(3) . ?
C16 C17 1.392(3) . ?
C17 C18 1.389(4) . ?
C17 H17 0.95 . ?
C18 C19 1.366(4) . ?
C18 H18 0.95 . ?
C19 C20 1.381(4) . ?
C19 H19 0.95 . ?
C20 C21 1.381(4) . ?
C20 H20 0.95 . ?
C21 H21 0.95 . ?
N1 N2 1.318(2) . ?
N2 N3 1.3413(19) . ?

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 C1 C6 118.55(16) . . ?
C2 C1 H1 120.7 . . ?
C6 C1 H1 120.7 . . ?
C1 C2 C3 121.24(17) . . ?
C1 C2 H2 119.4 . . ?
C3 C2 H2 119.4 . . ?
C4 C3 C2 121.12(16) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C5 C4 C3 116.65(15) . . ?
C5 C4 H4 121.7 . . ?
C3 C4 H4 121.7 . . ?
O1 C5 C4 126.29(13) . . ?
O1 C5 C6 110.13(13) . . ?
C4 C5 C6 123.56(15) . . ?
C1 C6 C5 118.85(14) . . ?
C1 C6 C7 135.57(14) . . ?
C5 C6 C7 105.57(14) . . ?
C8 C7 C6 106.86(13) . . ?
C8 C7 H7 126.6 . . ?
C6 C7 H7 126.6 . . ?
C7 C8 O1 111.13(14) . . ?
C7 C8 C9 133.36(14) . . ?
O1 C8 C9 115.45(12) . . ?
C8 C9 C10 113.44(12) . . ?
C8 C9 H9A 108.9 . . ?
C10 C9 H9A 108.9 . . ?
C8 C9 H9B 108.9 . . ?
C10 C9 H9B 108.9 . . ?
H9A C9 H9B 107.7 . . ?
C11 C10 C9 111.87(12) . . ?
C11 C10 H10A 109.2 . . ?
C9 C10 H10A 109.2 . . ?
C11 C10 H10B 109.2 . . ?
C9 C10 H10B 109.2 . . ?
H10A C10 H10B 107.9 . . ?
C10 C11 C12 112.28(13) . . ?
C10 C11 H11A 109.1 . . ?
C12 C11 H11A 109.1 . . ?
C10 C11 H11B 109.1 . . ?
C12 C11 H11B 109.1 . . ?
H11A C11 H11B 107.9 . . ?
C13 C12 C11 113.70(12) . . ?
C13 C12 H12A 108.8 . . ?
C11 C12 H12A 108.8 . . ?
C13 C12 H12B 108.8 . . ?
C11 C12 H12B 108.8 . . ?
H12A C12 H12B 107.7 . . ?
N1 C13 C14 107.87(14) . . ?
N1 C13 C12 122.10(13) . . ?
C14 C13 C12 129.98(14) . . ?
N3 C14 C13 104.91(14) . . ?
N3 C14 H14 127.5 . . ?
C13 C14 H14 127.5 . . ?
N3 C15 C16 112.04(14) . . ?
N3 C15 H15A 109.2 . . ?
C16 C15 H15A 109.2 . . ?
N3 C15 H15B 109.2 . . ?
C16 C15 H15B 109.2 . . ?
H15A C15 H15B 107.9 . . ?
C21 C16 C17 118.71(19) . . ?
C21 C16 C15 120.69(17) . . ?
C17 C16 C15 120.60(18) . . ?
C18 C17 C16 119.8(2) . . ?
C18 C17 H17 120.1 . . ?
C16 C17 H17 120.1 . . ?
C19 C18 C17 120.6(2) . . ?
C19 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
C18 C19 C20 120.2(2) . . ?
C18 C19 H19 119.9 . . ?
C20 C19 H19 119.9 . . ?
C21 C20 C19 119.5(2) . . ?
C21 C20 H20 120.3 . . ?
C19 C20 H20 120.3 . . ?
C20 C21 C16 121.1(2) . . ?
C20 C21 H21 119.4 . . ?
C16 C21 H21 119.4 . . ?
N2 N1 C13 109.16(13) . . ?
N1 N2 N3 106.85(13) . . ?
N2 N3 C14 111.21(14) . . ?
N2 N3 C15 120.57(15) . . ?
C14 N3 C15 128.21(14) . . ?
C5 O1 C8 106.29(11) . . ?
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_Faouzi12
_database_code_depnum_ccdc_archive 'CCDC 1020809'
_audit_update_record             
;
2014-08-22 deposited with the CCDC.
2015-01-30 downloaded from the CCDC.
;

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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C23 H16 O'
_chemical_formula_sum            'C23 H16 O'
_chemical_formula_weight         308.36
_chemical_compound_source        'synthesis as described'


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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_Int_Tables_number      4
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   11.008(3)
_cell_length_b                   7.5883(19)
_cell_length_c                   19.571(5)
_cell_angle_alpha                90
_cell_angle_beta                 90.988(10)
_cell_angle_gamma                90
_cell_volume                     1634.6(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    193(2)
_cell_measurement_reflns_used    714
_cell_measurement_theta_min      3.4
_cell_measurement_theta_max      20.54
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.02
_exptl_crystal_density_diffrn    1.253
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             648
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2008)'
_exptl_absorpt_correction_T_min  0.9930
_exptl_absorpt_correction_T_max  0.9985

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

_diffrn_ambient_temperature      193(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'microfocus sealed tube'
_diffrn_radiation_monochromator  'multilayer optics'
_diffrn_measurement_device_type  'Bruker Kappa APEX II Quazar'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_radiation_probe          x-ray
_diffrn_reflns_av_R_equivalents  0.08
_diffrn_reflns_av_unetI/netI     0.1425
_diffrn_reflns_number            11659
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.81
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_full        25.35
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_reflns_number_total             5736
_reflns_number_gt                2569
_reflns_threshold_expression     >2sigma(I)

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

_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_cell_refinement       'APEX2 and SAINT (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

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

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

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

_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)+(0.0563P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         5736
_refine_ls_number_parameters     433
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1856
_refine_ls_R_factor_gt           0.0704
_refine_ls_wR_factor_ref         0.172
_refine_ls_wR_factor_gt          0.1292
_refine_ls_goodness_of_fit_ref   0.972
_refine_ls_restrained_S_all      0.972
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.243
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.045

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

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C24 C 0.7849(5) 0.6126(9) -0.2693(3) 0.0448(17) Uani 1 1 d . . .
H24 H 0.8377 0.5445 -0.2409 0.054 Uiso 1 1 calc R . .
C25 C 0.7987(5) 0.6130(9) -0.3393(3) 0.0448(18) Uani 1 1 d . . .
H25 H 0.8614 0.5457 -0.3595 0.054 Uiso 1 1 calc R . .
C26 C 0.7197(5) 0.7129(10) -0.3801(3) 0.0474(17) Uani 1 1 d . . .
H26 H 0.7307 0.7173 -0.4281 0.057 Uiso 1 1 calc R . .
C27 C 0.6278(5) 0.8036(10) -0.3519(3) 0.056(2) Uani 1 1 d . . .
H27 H 0.572 0.8648 -0.3808 0.067 Uiso 1 1 calc R . .
C28 C 0.6129(5) 0.8096(8) -0.2831(3) 0.0437(17) Uani 1 1 d . . .
H28 H 0.5495 0.878 -0.2641 0.052 Uiso 1 1 calc R . .
C29 C 0.6925(5) 0.7133(9) -0.2406(3) 0.0366(15) Uani 1 1 d . . .
C30 C 0.6810(4) 0.7180(9) -0.1669(3) 0.0445(16) Uani 1 1 d . . .
C31 C 0.6690(5) 0.7212(10) -0.1067(3) 0.0405(16) Uani 1 1 d . . .
C32 C 0.6519(5) 0.7058(9) -0.0334(3) 0.0369(15) Uani 1 1 d . . .
C33 C 0.7429(5) 0.6286(9) 0.0069(3) 0.0385(16) Uani 1 1 d . . .
H33 H 0.8166 0.5913 -0.0132 0.046 Uiso 1 1 calc R . .
C34 C 0.7253(5) 0.6064(8) 0.0768(3) 0.0348(15) Uani 1 1 d . . .
H34 H 0.7867 0.5538 0.1048 0.042 Uiso 1 1 calc R . .
C35 C 0.6172(5) 0.6620(8) 0.1050(3) 0.0300(14) Uani 1 1 d . . .
C36 C 0.5269(5) 0.7373(9) 0.0633(3) 0.0350(15) Uani 1 1 d . . .
C37 C 0.5405(5) 0.7621(8) -0.0049(3) 0.0405(17) Uani 1 1 d . . .
H37 H 0.4783 0.8148 -0.0323 0.049 Uiso 1 1 calc R . .
C38 C 0.4187(5) 0.7769(10) 0.1060(3) 0.061(2) Uani 1 1 d . . .
H38A H 0.3937 0.9015 0.1007 0.074 Uiso 1 1 calc R . .
H38B H 0.3494 0.7002 0.0929 0.074 Uiso 1 1 calc R . .
C39 C 0.5759(5) 0.6656(9) 0.1755(3) 0.0422(18) Uani 1 1 d . . .
C40 C 0.6307(5) 0.6297(9) 0.2321(3) 0.0465(16) Uani 1 1 d . . .
H40 H 0.7067 0.5723 0.2271 0.056 Uiso 1 1 calc R . .
C41 C 0.5971(5) 0.6616(9) 0.3038(3) 0.0389(16) Uani 1 1 d . . .
C42 C 0.6681(5) 0.5829(9) 0.3540(3) 0.0480(18) Uani 1 1 d . . .
H42 H 0.7357 0.5129 0.3414 0.058 Uiso 1 1 calc R . .
C43 C 0.6423(5) 0.6047(9) 0.4225(3) 0.0516(19) Uani 1 1 d . . .
H43 H 0.6905 0.5451 0.456 0.062 Uiso 1 1 calc R . .
C44 C 0.5484(5) 0.7109(10) 0.4434(3) 0.0455(18) Uani 1 1 d . . .
H44 H 0.5332 0.7291 0.4905 0.055 Uiso 1 1 calc R . .
C45 C 0.4768(5) 0.7903(9) 0.3931(3) 0.0511(19) Uani 1 1 d . . .
H45 H 0.4109 0.8636 0.4057 0.061 Uiso 1 1 calc R . .
C46 C 0.5007(5) 0.7635(9) 0.3246(3) 0.0436(18) Uani 1 1 d . . .
H46 H 0.4494 0.8168 0.291 0.052 Uiso 1 1 calc R . .
O1 O 0.2894(3) 0.6393(6) 0.74108(17) 0.0464(11) Uani 1 1 d . . .
O2 O 0.4586(3) 0.7416(6) 0.17566(17) 0.0503(12) Uani 1 1 d . . .
C1 C 0.1545(5) 0.6392(8) 1.2080(3) 0.0444(16) Uani 1 1 d . . .
H1 H 0.2296 0.5931 1.1927 0.053 Uiso 1 1 calc R . .
C2 C 0.1269(5) 0.6345(10) 1.2773(3) 0.0445(17) Uani 1 1 d . . .
H2 H 0.1824 0.5798 1.3084 0.053 Uiso 1 1 calc R . .
C3 C 0.0200(5) 0.7078(9) 1.3024(3) 0.0435(16) Uani 1 1 d . . .
H3 H 0.0042 0.707 1.3499 0.052 Uiso 1 1 calc R . .
C4 C -0.0619(5) 0.7812(8) 1.2568(3) 0.0430(17) Uani 1 1 d . . .
H4 H -0.1362 0.8287 1.2724 0.052 Uiso 1 1 calc R . .
C5 C -0.0349(5) 0.7855(8) 1.1870(3) 0.0410(17) Uani 1 1 d . . .
H5 H -0.091 0.8406 1.1564 0.049 Uiso 1 1 calc R . .
C6 C 0.0705(5) 0.7128(9) 1.1605(3) 0.0372(15) Uani 1 1 d . . .
C7 C 0.0956(4) 0.7075(8) 1.0898(3) 0.0395(16) Uani 1 1 d . . .
C8 C 0.1089(5) 0.7042(11) 1.0301(3) 0.0444(16) Uani 1 1 d . . .
C9 C 0.1216(5) 0.7043(9) 0.9568(3) 0.0374(14) Uani 1 1 d . . .
C10 C 0.0264(5) 0.7723(8) 0.9146(3) 0.0392(16) Uani 1 1 d . . .
H10 H -0.0456 0.8141 0.9351 0.047 Uiso 1 1 calc R . .
C11 C 0.0359(5) 0.7790(7) 0.8452(3) 0.0338(15) Uani 1 1 d . . .
H11 H -0.0293 0.8235 0.8179 0.041 Uiso 1 1 calc R . .
C12 C 0.1401(4) 0.7213(8) 0.8155(2) 0.0290(14) Uani 1 1 d . . .
C13 C 0.2355(4) 0.6590(7) 0.8552(3) 0.0318(14) Uani 1 1 d . . .
C14 C 0.2270(5) 0.6452(8) 0.9254(3) 0.0423(16) Uani 1 1 d . . .
H14 H 0.2919 0.5963 0.9519 0.051 Uiso 1 1 calc R . .
C15 C 0.3369(5) 0.6091(9) 0.8107(3) 0.0478(18) Uani 1 1 d . . .
H15A H 0.4092 0.6834 0.8201 0.057 Uiso 1 1 calc R . .
H15B H 0.3593 0.4839 0.8174 0.057 Uiso 1 1 calc R . .
C16 C 0.1732(4) 0.7074(8) 0.7445(2) 0.0317(13) Uani 1 1 d . . .
C17 C 0.1063(4) 0.7469(8) 0.6891(3) 0.0365(14) Uani 1 1 d . . .
H17 H 0.0293 0.7968 0.6987 0.044 Uiso 1 1 calc R . .
C18 C 0.1303(4) 0.7269(9) 0.6156(3) 0.0361(15) Uani 1 1 d . . .
C19 C 0.2271(5) 0.6246(10) 0.5921(3) 0.0509(18) Uani 1 1 d . . .
H19 H 0.2787 0.5648 0.6239 0.061 Uiso 1 1 calc R . .
C20 C 0.2477(5) 0.6109(10) 0.5227(3) 0.057(2) Uani 1 1 d . . .
H20 H 0.3128 0.5407 0.5068 0.069 Uiso 1 1 calc R . .
C21 C 0.1723(6) 0.7006(11) 0.4762(3) 0.062(2) Uani 1 1 d . . .
H21 H 0.1876 0.695 0.4286 0.075 Uiso 1 1 calc R . .
C22 C 0.0761(5) 0.7967(9) 0.4997(3) 0.055(2) Uani 1 1 d . . .
H22 H 0.0236 0.8546 0.4679 0.066 Uiso 1 1 calc R . .
C23 C 0.0544(5) 0.8109(8) 0.5689(3) 0.0431(17) Uani 1 1 d . . .
H23 H -0.0125 0.8782 0.5843 0.052 Uiso 1 1 calc R . .



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

_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
C24 C25 1.381(7) . ?
C24 C29 1.398(8) . ?
C24 H24 0.95 . ?
C25 C26 1.395(8) . ?
C25 H25 0.95 . ?
C26 C27 1.350(8) . ?
C26 H26 0.95 . ?
C27 C28 1.359(8) . ?
C27 H27 0.95 . ?
C28 C29 1.404(7) . ?
C28 H28 0.95 . ?
C29 C30 1.450(7) . ?
C30 C31 1.187(7) . ?
C31 C32 1.455(7) . ?
C32 C33 1.394(7) . ?
C32 C37 1.422(7) . ?
C33 C34 1.397(7) . ?
C33 H33 0.95 . ?
C34 C35 1.386(7) . ?
C34 H34 0.95 . ?
C35 C36 1.398(7) . ?
C35 C39 1.460(7) . ?
C36 C37 1.360(7) . ?
C36 C38 1.497(7) . ?
C37 H37 0.95 . ?
C38 O2 1.450(6) . ?
C38 H38A 0.99 . ?
C38 H38B 0.99 . ?
C39 C40 1.281(7) . ?
C39 O2 1.414(6) . ?
C40 C41 1.477(7) . ?
C40 H40 0.95 . ?
C41 C46 1.379(8) . ?
C41 C42 1.381(8) . ?
C42 C43 1.386(7) . ?
C42 H42 0.95 . ?
C43 C44 1.378(8) . ?
C43 H43 0.95 . ?
C44 C45 1.387(8) . ?
C44 H44 0.95 . ?
C45 C46 1.386(7) . ?
C45 H45 0.95 . ?
C46 H46 0.95 . ?
O1 C16 1.382(6) . ?
O1 C15 1.469(6) . ?
C1 C2 1.396(7) . ?
C1 C6 1.415(7) . ?
C1 H1 0.95 . ?
C2 C3 1.399(7) . ?
C2 H2 0.95 . ?
C3 C4 1.375(7) . ?
C3 H3 0.95 . ?
C4 C5 1.403(7) . ?
C4 H4 0.95 . ?
C5 C6 1.392(7) . ?
C5 H5 0.95 . ?
C6 C7 1.416(7) . ?
C7 C8 1.180(7) . ?
C8 C9 1.445(7) . ?
C9 C14 1.397(7) . ?
C9 C10 1.420(7) . ?
C10 C11 1.364(7) . ?
C10 H10 0.95 . ?
C11 C12 1.368(6) . ?
C11 H11 0.95 . ?
C12 C13 1.379(6) . ?
C12 C16 1.445(6) . ?
C13 C14 1.384(7) . ?
C13 C15 1.476(7) . ?
C14 H14 0.95 . ?
C15 H15A 0.99 . ?
C15 H15B 0.99 . ?
C16 C17 1.335(6) . ?
C17 C18 1.475(7) . ?
C17 H17 0.95 . ?
C18 C23 1.383(7) . ?
C18 C19 1.402(8) . ?
C19 C20 1.385(7) . ?
C19 H19 0.95 . ?
C20 C21 1.398(8) . ?
C20 H20 0.95 . ?
C21 C22 1.371(8) . ?
C21 H21 0.95 . ?
C22 C23 1.384(7) . ?
C22 H22 0.95 . ?
C23 H23 0.95 . ?

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
C25 C24 C29 119.4(6) . . ?
C25 C24 H24 120.3 . . ?
C29 C24 H24 120.3 . . ?
C24 C25 C26 119.4(6) . . ?
C24 C25 H25 120.3 . . ?
C26 C25 H25 120.3 . . ?
C27 C26 C25 120.5(6) . . ?
C27 C26 H26 119.8 . . ?
C25 C26 H26 119.8 . . ?
C26 C27 C28 121.8(6) . . ?
C26 C27 H27 119.1 . . ?
C28 C27 H27 119.1 . . ?
C27 C28 C29 119.0(6) . . ?
C27 C28 H28 120.5 . . ?
C29 C28 H28 120.5 . . ?
C24 C29 C28 119.8(5) . . ?
C24 C29 C30 119.4(5) . . ?
C28 C29 C30 120.8(6) . . ?
C31 C30 C29 178.6(6) . . ?
C30 C31 C32 174.1(8) . . ?
C33 C32 C37 121.4(5) . . ?
C33 C32 C31 119.2(5) . . ?
C37 C32 C31 119.4(5) . . ?
C32 C33 C34 119.7(5) . . ?
C32 C33 H33 120.2 . . ?
C34 C33 H33 120.2 . . ?
C35 C34 C33 119.2(5) . . ?
C35 C34 H34 120.4 . . ?
C33 C34 H34 120.4 . . ?
C34 C35 C36 119.9(5) . . ?
C34 C35 C39 131.7(5) . . ?
C36 C35 C39 108.3(5) . . ?
C37 C36 C35 122.7(5) . . ?
C37 C36 C38 128.5(5) . . ?
C35 C36 C38 108.7(5) . . ?
C36 C37 C32 117.0(6) . . ?
C36 C37 H37 121.5 . . ?
C32 C37 H37 121.5 . . ?
O2 C38 C36 104.8(4) . . ?
O2 C38 H38A 110.8 . . ?
C36 C38 H38A 110.8 . . ?
O2 C38 H38B 110.8 . . ?
C36 C38 H38B 110.8 . . ?
H38A C38 H38B 108.9 . . ?
C40 C39 O2 120.1(5) . . ?
C40 C39 C35 131.5(5) . . ?
O2 C39 C35 107.9(5) . . ?
C39 C40 C41 131.6(6) . . ?
C39 C40 H40 114.2 . . ?
C41 C40 H40 114.2 . . ?
C46 C41 C42 117.5(5) . . ?
C46 C41 C40 125.4(6) . . ?
C42 C41 C40 117.1(6) . . ?
C41 C42 C43 120.9(6) . . ?
C41 C42 H42 119.5 . . ?
C43 C42 H42 119.5 . . ?
C44 C43 C42 121.5(6) . . ?
C44 C43 H43 119.2 . . ?
C42 C43 H43 119.2 . . ?
C43 C44 C45 117.7(6) . . ?
C43 C44 H44 121.2 . . ?
C45 C44 H44 121.2 . . ?
C46 C45 C44 120.5(6) . . ?
C46 C45 H45 119.8 . . ?
C44 C45 H45 119.8 . . ?
C41 C46 C45 121.8(6) . . ?
C41 C46 H46 119.1 . . ?
C45 C46 H46 119.1 . . ?
C16 O1 C15 109.2(4) . . ?
C39 O2 C38 109.6(4) . . ?
C2 C1 C6 119.8(5) . . ?
C2 C1 H1 120.1 . . ?
C6 C1 H1 120.1 . . ?
C1 C2 C3 121.9(6) . . ?
C1 C2 H2 119 . . ?
C3 C2 H2 119 . . ?
C4 C3 C2 118.7(6) . . ?
C4 C3 H3 120.7 . . ?
C2 C3 H3 120.7 . . ?
C3 C4 C5 119.6(6) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C6 C5 C4 123.0(6) . . ?
C6 C5 H5 118.5 . . ?
C4 C5 H5 118.5 . . ?
C5 C6 C1 116.9(5) . . ?
C5 C6 C7 123.5(6) . . ?
C1 C6 C7 119.6(6) . . ?
C8 C7 C6 175.9(6) . . ?
C7 C8 C9 178.0(7) . . ?
C14 C9 C10 118.1(5) . . ?
C14 C9 C8 122.1(5) . . ?
C10 C9 C8 119.7(5) . . ?
C11 C10 C9 121.6(5) . . ?
C11 C10 H10 119.2 . . ?
C9 C10 H10 119.2 . . ?
C10 C11 C12 119.4(5) . . ?
C10 C11 H11 120.3 . . ?
C12 C11 H11 120.3 . . ?
C11 C12 C13 120.4(5) . . ?
C11 C12 C16 131.3(5) . . ?
C13 C12 C16 108.3(5) . . ?
C12 C13 C14 121.5(5) . . ?
C12 C13 C15 109.4(5) . . ?
C14 C13 C15 129.1(5) . . ?
C13 C14 C9 118.9(6) . . ?
C13 C14 H14 120.5 . . ?
C9 C14 H14 120.6 . . ?
O1 C15 C13 104.2(4) . . ?
O1 C15 H15A 110.9 . . ?
C13 C15 H15A 110.9 . . ?
O1 C15 H15B 110.9 . . ?
C13 C15 H15B 110.9 . . ?
H15A C15 H15B 108.9 . . ?
C17 C16 O1 122.9(5) . . ?
C17 C16 C12 128.3(5) . . ?
O1 C16 C12 108.9(4) . . ?
C16 C17 C18 131.6(5) . . ?
C16 C17 H17 114.2 . . ?
C18 C17 H17 114.2 . . ?
C23 C18 C19 119.5(5) . . ?
C23 C18 C17 118.8(5) . . ?
C19 C18 C17 121.7(5) . . ?
C20 C19 C18 120.1(6) . . ?
C20 C19 H19 120 . . ?
C18 C19 H19 120 . . ?
C19 C20 C21 119.8(6) . . ?
C19 C20 H20 120.1 . . ?
C21 C20 H20 120.1 . . ?
C22 C21 C20 119.6(6) . . ?
C22 C21 H21 120.2 . . ?
C20 C21 H21 120.2 . . ?
C21 C22 C23 121.1(6) . . ?
C21 C22 H22 119.4 . . ?
C23 C22 H22 119.4 . . ?
C18 C23 C22 119.9(6) . . ?
C18 C23 H23 120 . . ?
C22 C23 H23 120 . . ?
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_faouzi16m
_database_code_depnum_ccdc_archive 'CCDC 1020810'
_audit_update_record             
;
2014-08-22 deposited with the CCDC.
2015-01-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H23 N O2'
_chemical_formula_weight         333.41

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           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.1264(5)
_cell_length_b                   9.7169(6)
_cell_length_c                   10.2731(7)
_cell_angle_alpha                95.504(4)
_cell_angle_beta                 91.157(4)
_cell_angle_gamma                101.221(4)
_cell_volume                     888.78(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    193(2)
_cell_measurement_reflns_used    3436
_cell_measurement_theta_min      2.805
_cell_measurement_theta_max      24.767

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.246
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             356
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9843
_exptl_absorpt_correction_T_max  0.9937
_exptl_absorpt_process_details   'SADABS (Bruker-AXS)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      193(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_reflns_number            13707
_diffrn_reflns_av_R_equivalents  0.0591
_diffrn_reflns_av_sigmaI/netI    0.0582
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         5.25
_diffrn_reflns_theta_max         26.37
_reflns_number_total             3588
_reflns_number_gt                2615
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.1144P)²+0.4739P] 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         3588
_refine_ls_number_parameters     227
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0822
_refine_ls_R_factor_gt           0.0587
_refine_ls_wR_factor_ref         0.2170
_refine_ls_wR_factor_gt          0.1776
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_restrained_S_all      1.079
_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 0.4725(2) 0.60398(19) 0.30343(18) 0.0287(4) Uani 1 1 d . . .
O1 O 0.38717(19) 0.79027(17) 0.41497(16) 0.0371(4) Uani 1 1 d . . .
O2 O 0.2627(2) -0.07864(18) 0.11011(18) 0.0445(5) Uani 1 1 d . . .
C1 C 0.4874(3) 0.7404(2) 0.3625(2) 0.0298(5) Uani 1 1 d . . .
C2 C 0.6080(2) 0.5787(2) 0.2506(2) 0.0271(5) Uani 1 1 d . . .
C3 C 0.7160(3) 0.7135(2) 0.2793(2) 0.0302(5) Uani 1 1 d . . .
C4 C 0.6452(3) 0.8103(2) 0.3482(2) 0.0298(5) Uani 1 1 d . . .
C5 C 0.7187(3) 0.9460(3) 0.3922(2) 0.0372(6) Uani 1 1 d . . .
H5 H 0.6688 1.0106 0.4398 0.045 Uiso 1 1 calc R . .
C6 C 0.8677(3) 0.9832(3) 0.3638(3) 0.0438(6) Uani 1 1 d . . .
H6 H 0.9219 1.0751 0.3931 0.053 Uiso 1 1 calc R . .
C7 C 0.9396(3) 0.8880(3) 0.2930(3) 0.0445(6) Uani 1 1 d . . .
H7 H 1.0418 0.9166 0.2739 0.053 Uiso 1 1 calc R . .
C8 C 0.8646(3) 0.7517(3) 0.2495(2) 0.0369(6) Uani 1 1 d . . .
H8 H 0.9139 0.6871 0.2010 0.044 Uiso 1 1 calc R . .
C9 C 0.3271(2) 0.5034(2) 0.2876(2) 0.0288(5) Uani 1 1 d . . .
H9 H 0.3469 0.4144 0.2405 0.035 Uiso 1 1 calc R . .
C10 C 0.2149(3) 0.5546(3) 0.2017(2) 0.0351(5) Uani 1 1 d . . .
H10A H 0.2600 0.5791 0.1180 0.042 Uiso 1 1 calc R . .
H10B H 0.1866 0.6400 0.2464 0.042 Uiso 1 1 calc R . .
C11 C 0.0769(3) 0.4374(3) 0.1754(2) 0.0382(6) Uani 1 1 d . . .
H11A H 0.1049 0.3550 0.1251 0.046 Uiso 1 1 calc R . .
H11B H 0.0019 0.4707 0.1219 0.046 Uiso 1 1 calc R . .
C12 C 0.0082(3) 0.3930(3) 0.3029(3) 0.0389(6) Uani 1 1 d . . .
H12A H -0.0301 0.4725 0.3485 0.047 Uiso 1 1 calc R . .
H12B H -0.0773 0.3131 0.2829 0.047 Uiso 1 1 calc R . .
C13 C 0.1222(3) 0.3493(3) 0.3918(3) 0.0431(6) Uani 1 1 d . . .
H13A H 0.1505 0.2623 0.3509 0.052 Uiso 1 1 calc R . .
H13B H 0.0768 0.3283 0.4762 0.052 Uiso 1 1 calc R . .
C14 C 0.2625(3) 0.4653(3) 0.4172(2) 0.0407(6) Uani 1 1 d . . .
H14A H 0.2367 0.5496 0.4662 0.049 Uiso 1 1 calc R . .
H14B H 0.3374 0.4318 0.4706 0.049 Uiso 1 1 calc R . .
C15 C 0.6388(3) 0.4603(2) 0.1893(2) 0.0318(5) Uani 1 1 d . . .
H15 H 0.7366 0.4687 0.1569 0.038 Uiso 1 1 calc R . .
C16 C 0.5426(3) 0.3177(2) 0.1646(2) 0.0301(5) Uani 1 1 d . . .
C17 C 0.5198(3) 0.2276(2) 0.2636(2) 0.0342(5) Uani 1 1 d . . .
H17 H 0.5693 0.2569 0.3467 0.041 Uiso 1 1 calc R . .
C18 C 0.4265(3) 0.0965(2) 0.2428(2) 0.0364(6) Uani 1 1 d . . .
H18 H 0.4118 0.0369 0.3115 0.044 Uiso 1 1 calc R . .
C19 C 0.3541(3) 0.0517(2) 0.1209(2) 0.0323(5) Uani 1 1 d . . .
C20 C 0.3782(3) 0.1382(3) 0.0205(2) 0.0366(6) Uani 1 1 d . . .
H20 H 0.3307 0.1080 -0.0633 0.044 Uiso 1 1 calc R . .
C21 C 0.4722(3) 0.2693(3) 0.0437(2) 0.0350(5) Uani 1 1 d . . .
H21 H 0.4888 0.3277 -0.0258 0.042 Uiso 1 1 calc R . .
C22 C 0.1854(3) -0.1266(3) -0.0121(3) 0.0517(7) Uani 1 1 d . . .
H22A H 0.1188 -0.0627 -0.0313 0.077 Uiso 1 1 calc R . .
H22B H 0.1264 -0.2218 -0.0083 0.077 Uiso 1 1 calc R . .
H22C H 0.2578 -0.1286 -0.0811 0.077 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 C1 1.385(3) . ?
N1 C2 1.415(3) . ?
N1 C9 1.483(3) . ?
O1 C1 1.227(3) . ?
O2 C19 1.367(3) . ?
O2 C22 1.420(3) . ?
C1 C4 1.484(3) . ?
C2 C15 1.340(3) . ?
C2 C3 1.478(3) . ?
C3 C8 1.383(3) . ?
C3 C4 1.389(3) . ?
C4 C5 1.387(3) . ?
C5 C6 1.382(4) . ?
C6 C7 1.394(4) . ?
C7 C8 1.395(4) . ?
C9 C14 1.517(3) . ?
C9 C10 1.523(3) . ?
C10 C11 1.525(3) . ?
C11 C12 1.527(3) . ?
C12 C13 1.518(4) . ?
C13 C14 1.532(3) . ?
C15 C16 1.485(3) . ?
C16 C21 1.384(3) . ?
C16 C17 1.398(3) . ?
C17 C18 1.382(3) . ?
C18 C19 1.394(3) . ?
C19 C20 1.386(3) . ?
C20 C21 1.387(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C2 111.86(18) . . ?
C1 N1 C9 122.79(18) . . ?
C2 N1 C9 125.09(17) . . ?
C19 O2 C22 117.2(2) . . ?
O1 C1 N1 125.3(2) . . ?
O1 C1 C4 128.4(2) . . ?
N1 C1 C4 106.34(18) . . ?
C15 C2 N1 129.5(2) . . ?
C15 C2 C3 125.3(2) . . ?
N1 C2 C3 105.21(17) . . ?
C8 C3 C4 120.2(2) . . ?
C8 C3 C2 131.0(2) . . ?
C4 C3 C2 108.78(19) . . ?
C5 C4 C3 122.5(2) . . ?
C5 C4 C1 129.7(2) . . ?
C3 C4 C1 107.79(19) . . ?
C6 C5 C4 117.1(2) . . ?
C5 C6 C7 121.0(2) . . ?
C6 C7 C8 121.4(2) . . ?
C3 C8 C7 117.8(2) . . ?
N1 C9 C14 112.83(19) . . ?
N1 C9 C10 112.07(18) . . ?
C14 C9 C10 111.59(19) . . ?
C9 C10 C11 108.71(19) . . ?
C10 C11 C12 111.3(2) . . ?
C13 C12 C11 111.2(2) . . ?
C12 C13 C14 111.5(2) . . ?
C9 C14 C13 109.3(2) . . ?
C2 C15 C16 129.5(2) . . ?
C21 C16 C17 117.6(2) . . ?
C21 C16 C15 121.6(2) . . ?
C17 C16 C15 120.8(2) . . ?
C18 C17 C16 121.2(2) . . ?
C17 C18 C19 120.0(2) . . ?
O2 C19 C20 124.6(2) . . ?
O2 C19 C18 115.8(2) . . ?
C20 C19 C18 119.7(2) . . ?
C19 C20 C21 119.4(2) . . ?
C16 C21 C20 122.2(2) . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        26.37
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.326
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.063
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_faouzi18m
_database_code_depnum_ccdc_archive 'CCDC 1020811'
_audit_update_record             
;
2014-08-22 deposited with the CCDC.
2015-01-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H18 N4 O2'
_chemical_formula_weight         346.38

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           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.6257(7)
_cell_length_b                   19.7469(19)
_cell_length_c                   23.768(2)
_cell_angle_alpha                79.737(6)
_cell_angle_beta                 88.280(7)
_cell_angle_gamma                82.746(7)
_cell_volume                     2577.2(5)
_cell_formula_units_Z            6
_cell_measurement_temperature    193(2)
_cell_measurement_reflns_used    2684
_cell_measurement_theta_min      2.49
_cell_measurement_theta_max      20.06

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1092
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9651
_exptl_absorpt_correction_T_max  0.9973
_exptl_absorpt_process_details   'SADABS (Bruker-AXS)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      193(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         micro-focus
_diffrn_radiation_monochromator  'multilayer optics'
_diffrn_measurement_device_type  'Bruker kappa APEX-II CCD Quazar'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            44315
_diffrn_reflns_av_R_equivalents  0.1375
_diffrn_reflns_av_sigmaI/netI    0.1284
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         5.15
_diffrn_reflns_theta_max         24.71
_reflns_number_total             8707
_reflns_number_gt                4909
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0000P)²+3.4849P] 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         8707
_refine_ls_number_parameters     758
_refine_ls_number_restraints     200
_refine_ls_R_factor_all          0.1470
_refine_ls_R_factor_gt           0.0759
_refine_ls_wR_factor_ref         0.1814
_refine_ls_wR_factor_gt          0.1565
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_restrained_S_all      1.065
_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 0.2966(6) 0.45338(16) 0.36515(12) 0.0463(8) Uani 1 1 d . . .
O2 O 1.0298(6) 0.32286(15) 0.37015(12) 0.0473(8) Uani 1 1 d . . .
N1 N 0.6616(6) 0.38592(17) 0.38273(13) 0.0333(9) Uani 1 1 d . . .
N2 N 1.2014(6) 0.36541(18) 0.55649(14) 0.0364(9) Uani 1 1 d . . .
N3 N 1.3086(6) 0.30706(19) 0.58635(14) 0.0366(9) Uani 1 1 d . . .
N4 N 1.1353(6) 0.26817(17) 0.60667(13) 0.0300(8) Uani 1 1 d . . .
C1 C 0.4778(9) 0.4233(2) 0.34779(17) 0.0342(10) Uani 1 1 d . . .
C2 C 0.8489(8) 0.3589(2) 0.35045(18) 0.0346(10) Uani 1 1 d . . .
C3 C 0.7807(8) 0.3817(2) 0.28968(16) 0.0325(10) Uani 1 1 d . . .
C4 C 0.5565(8) 0.4189(2) 0.28797(16) 0.0303(10) Uani 1 1 d . . .
C5 C 0.4432(8) 0.4461(2) 0.23688(17) 0.0377(11) Uani 1 1 d . . .
H5 H 0.2875 0.4713 0.2356 0.045 Uiso 1 1 calc R . .
C6 C 0.5678(10) 0.4349(2) 0.18722(18) 0.0455(13) Uani 1 1 d . . .
H6 H 0.4949 0.4528 0.1512 0.055 Uiso 1 1 calc R . .
C7 C 0.7931(9) 0.3986(2) 0.18880(18) 0.0442(12) Uani 1 1 d . . .
H7 H 0.8743 0.3927 0.1541 0.053 Uiso 1 1 calc R . .
C8 C 0.9035(9) 0.3704(2) 0.24072(18) 0.0412(12) Uani 1 1 d . . .
H8 H 1.0578 0.3444 0.2423 0.049 Uiso 1 1 calc R . .
C9 C 0.6633(8) 0.3781(2) 0.44464(16) 0.0365(11) Uani 1 1 d . . .
H9A H 0.7462 0.3317 0.4607 0.044 Uiso 1 1 calc R . .
H9B H 0.4961 0.3805 0.4591 0.044 Uiso 1 1 calc R . .
C10 C 0.7860(8) 0.4328(2) 0.46529(16) 0.0340(10) Uani 1 1 d . . .
H10A H 0.7018 0.4792 0.4497 0.041 Uiso 1 1 calc R . .
H10B H 0.9527 0.4307 0.4505 0.041 Uiso 1 1 calc R . .
C11 C 0.7893(8) 0.4234(2) 0.53030(16) 0.0347(10) Uani 1 1 d . . .
H11A H 0.8316 0.4664 0.5413 0.042 Uiso 1 1 calc R . .
H11B H 0.6258 0.4169 0.5451 0.042 Uiso 1 1 calc R . .
C12 C 0.9599(7) 0.3636(2) 0.55842(15) 0.0283(10) Uani 1 1 d . . .
C13 C 0.9180(7) 0.3011(2) 0.59004(16) 0.0307(10) Uani 1 1 d . . .
H13 H 0.7673 0.2845 0.5984 0.037 Uiso 1 1 calc R . .
C14 C 1.1973(8) 0.2003(2) 0.64229(17) 0.0378(11) Uani 1 1 d . . .
H14A H 1.3739 0.1890 0.6429 0.045 Uiso 1 1 calc R . .
H14B H 1.1302 0.1649 0.6250 0.045 Uiso 1 1 calc R . .
C15 C 1.1054(8) 0.1967(2) 0.70317(17) 0.0323(10) Uani 1 1 d . . .
C16 C 1.2242(9) 0.2240(2) 0.74218(19) 0.0505(13) Uani 1 1 d . . .
H16 H 1.3615 0.2465 0.7302 0.061 Uiso 1 1 calc R . .
C17 C 1.1473(12) 0.2194(3) 0.7981(2) 0.0659(17) Uani 1 1 d . . .
H17 H 1.2322 0.2383 0.8243 0.079 Uiso 1 1 calc R . .
C18 C 0.9487(12) 0.1876(2) 0.8160(2) 0.0597(16) Uani 1 1 d . . .
H18 H 0.8946 0.1848 0.8545 0.072 Uiso 1 1 calc R . .
C19 C 0.8285(10) 0.1598(2) 0.7779(2) 0.0541(14) Uani 1 1 d . . .
H19 H 0.6910 0.1375 0.7901 0.065 Uiso 1 1 calc R . .
C20 C 0.9088(9) 0.1643(2) 0.72110(19) 0.0448(12) Uani 1 1 d . . .
H20 H 0.8261 0.1447 0.6949 0.054 Uiso 1 1 calc R . .
O3 O 0.1632(5) 0.90282(15) 0.39829(11) 0.0414(8) Uani 1 1 d . . .
O4 O 0.7442(5) 1.03200(15) 0.43191(12) 0.0435(8) Uani 1 1 d . . .
N5 N 0.4288(6) 0.98101(16) 0.40504(13) 0.0299(8) Uani 1 1 d . . .
N6 N 0.4539(6) 0.99663(19) 0.18961(14) 0.0426(10) Uani 1 1 d . . .
N7 N 0.5345(7) 0.9904(2) 0.13747(14) 0.0456(10) Uani 1 1 d . . .
N8 N 0.7712(7) 0.99121(17) 0.13805(13) 0.0342(9) Uani 1 1 d . . .
C21 C 0.3371(8) 0.9177(2) 0.42042(16) 0.0309(10) Uani 1 1 d . . .
C22 C 0.6303(8) 0.9831(2) 0.43695(16) 0.0325(10) Uani 1 1 d . . .
C23 C 0.6703(7) 0.9146(2) 0.47573(15) 0.0294(10) Uani 1 1 d . . .
C24 C 0.4955(7) 0.8759(2) 0.46597(15) 0.0282(10) Uani 1 1 d . . .
C25 C 0.4856(8) 0.8096(2) 0.49480(16) 0.0368(11) Uani 1 1 d . . .
H25 H 0.3635 0.7833 0.4874 0.044 Uiso 1 1 calc R . .
C26 C 0.6610(8) 0.7826(2) 0.53508(17) 0.0411(11) Uani 1 1 d . . .
H26 H 0.6605 0.7367 0.5557 0.049 Uiso 1 1 calc R . .
C27 C 0.8375(8) 0.8217(2) 0.54581(17) 0.0426(12) Uani 1 1 d . . .
H27 H 0.9548 0.8023 0.5740 0.051 Uiso 1 1 calc R . .
C28 C 0.8465(8) 0.8893(2) 0.51605(16) 0.0354(11) Uani 1 1 d . . .
H28 H 0.9671 0.9162 0.5232 0.042 Uiso 1 1 calc R . .
C29 C 0.3181(8) 1.0382(2) 0.36242(16) 0.0376(11) Uani 1 1 d . . .
H29A H 0.3882 1.0810 0.3654 0.045 Uiso 1 1 calc R . .
H29B H 0.1444 1.0463 0.3708 0.045 Uiso 1 1 calc R . .
C30 C 0.3531(8) 1.0241(2) 0.30149(16) 0.0346(10) Uani 1 1 d . . .
H30A H 0.2669 0.9845 0.2975 0.042 Uiso 1 1 calc R . .
H30B H 0.2796 1.0651 0.2747 0.042 Uiso 1 1 calc R . .
C31 C 0.6103(8) 1.0081(2) 0.28435(17) 0.0399(11) Uani 1 1 d . . .
H31A H 0.7008 1.0452 0.2922 0.048 Uiso 1 1 calc R . .
H31B H 0.6792 0.9640 0.3082 0.048 Uiso 1 1 calc R . .
C32 C 0.6423(8) 1.0018(2) 0.22249(17) 0.0323(10) Uani 1 1 d . . .
C33 C 0.8445(8) 0.9988(2) 0.18939(16) 0.0343(10) Uani 1 1 d . . .
H33 H 1.0035 1.0014 0.2004 0.041 Uiso 1 1 calc R . .
C34 C 0.9115(9) 0.9883(2) 0.08567(16) 0.0395(11) Uani 1 1 d . . .
H34A H 0.8485 0.9558 0.0642 0.047 Uiso 1 1 calc R . .
H34B H 1.0802 0.9704 0.0956 0.047 Uiso 1 1 calc R . .
C35 C 0.9019(8) 1.0592(2) 0.04817(16) 0.0346(10) Uani 1 1 d . . .
C36 C 1.0792(9) 1.1005(2) 0.05124(18) 0.0458(12) Uani 1 1 d . . .
H36 H 1.2109 1.0840 0.0761 0.055 Uiso 1 1 calc R . .
C37 C 1.0660(11) 1.1663(3) 0.0180(2) 0.0570(14) Uani 1 1 d . . .
H37 H 1.1891 1.1944 0.0205 0.068 Uiso 1 1 calc R . .
C38 C 0.8806(11) 1.1909(3) -0.0178(2) 0.0616(15) Uani 1 1 d . . .
H38 H 0.8738 1.2361 -0.0400 0.074 Uiso 1 1 calc R . .
C39 C 0.7017(10) 1.1508(3) -0.0223(2) 0.0623(15) Uani 1 1 d . . .
H39 H 0.5717 1.1680 -0.0476 0.075 Uiso 1 1 calc R . .
C40 C 0.7134(9) 1.0837(3) 0.01123(18) 0.0513(13) Uani 1 1 d . . .
H40 H 0.5913 1.0554 0.0083 0.062 Uiso 1 1 calc R . .
O5 O 0.3672(7) 0.68339(17) 1.11744(13) 0.0591(10) Uani 1 1 d . . .
O6 O 1.0888(6) 0.55121(17) 1.15340(12) 0.0499(9) Uani 1 1 d . . .
N9 N 0.7401(7) 0.62001(18) 1.12142(13) 0.0371(9) Uani 1 1 d . . .
C41 C 0.5323(9) 0.6476(2) 1.14485(18) 0.0408(12) Uani 1 1 d . . .
C42 C 0.8985(9) 0.5824(2) 1.16320(17) 0.0373(11) Uani 1 1 d . . .
C43 C 0.7763(8) 0.5892(2) 1.21919(17) 0.0348(11) Uani 1 1 d . . .
C44 C 0.5542(8) 0.6266(2) 1.20803(17) 0.0356(11) Uani 1 1 d . . .
C45 C 0.3982(9) 0.6396(2) 1.25149(19) 0.0467(12) Uani 1 1 d . . .
H45 H 0.2456 0.6658 1.2437 0.056 Uiso 1 1 calc R . .
C46 C 0.4709(10) 0.6132(2) 1.30685(19) 0.0466(12) Uani 1 1 d . . .
H46 H 0.3644 0.6200 1.3377 0.056 Uiso 1 1 calc R . .
C47 C 0.6948(10) 0.5772(2) 1.31817(18) 0.0437(12) Uani 1 1 d . . .
H47 H 0.7424 0.5611 1.3567 0.052 Uiso 1 1 calc R . .
C48 C 0.8533(9) 0.5638(2) 1.27418(17) 0.0428(12) Uani 1 1 d . . .
H48 H 1.0073 0.5383 1.2818 0.051 Uiso 1 1 calc R . .
C49 C 0.7892(9) 0.6267(2) 1.06033(16) 0.0410(12) Uani 1 1 d . C .
H49A H 0.9646 0.6217 1.0537 0.049 Uiso 1 1 calc R . .
H49B H 0.7218 0.6734 1.0409 0.049 Uiso 1 1 calc R . .
C50 C 0.6818(9) 0.5723(2) 1.03489(18) 0.0472(13) Uani 1 1 d D . .
H50A H 0.5083 0.5765 1.0441 0.057 Uiso 1 1 calc R A 1
H50B H 0.7534 0.5261 1.0547 0.057 Uiso 1 1 calc R A 1
C54 C 0.3893(9) 0.8055(2) 0.85597(18) 0.0454(12) Uani 1 1 d D . .
H54A H 0.5215 0.8328 0.8602 0.054 Uiso 1 1 calc R B 1
H54B H 0.2393 0.8303 0.8688 0.054 Uiso 1 1 calc R B 1
C51 C 0.710(3) 0.5736(7) 0.9707(5) 0.035(3) Uani 0.494(5) 1 d PDU C 1
H51A H 0.8816 0.5708 0.9600 0.042 Uiso 0.494(5) 1 calc PR C 1
H51B H 0.6450 0.5331 0.9605 0.042 Uiso 0.494(5) 1 calc PR C 1
C52 C 0.5808(17) 0.6378(5) 0.9392(4) 0.0364(19) Uani 0.494(5) 1 d PDU C 1
C53 C 0.6441(17) 0.6978(5) 0.9110(4) 0.0378(16) Uani 0.494(5) 1 d PDU C 1
H53 H 0.8017 0.7104 0.9051 0.045 Uiso 0.494(5) 1 calc PR C 1
N12 N 0.4360(15) 0.7369(4) 0.8924(4) 0.0342(19) Uani 0.494(5) 1 d PDU C 1
N11 N 0.2517(14) 0.7028(4) 0.9109(3) 0.0419(18) Uani 0.494(5) 1 d PDU C 1
N10 N 0.3400(14) 0.6416(4) 0.9400(3) 0.0413(18) Uani 0.494(5) 1 d PDU C 1
C51' C 0.757(3) 0.5819(7) 0.9720(4) 0.036(3) Uani 0.506(5) 1 d PDU C 2
H51C H 0.9338 0.5725 0.9703 0.043 Uiso 0.506(5) 1 calc PR C 2
H51D H 0.6920 0.5460 0.9548 0.043 Uiso 0.506(5) 1 calc PR C 2
C52' C 0.6842(17) 0.6498(5) 0.9359(4) 0.0354(19) Uani 0.506(5) 1 d PDU C 2
C53' C 0.4782(17) 0.6873(5) 0.9172(4) 0.0392(16) Uani 0.506(5) 1 d PDU C 2
H53' H 0.3216 0.6740 0.9232 0.047 Uiso 0.506(5) 1 calc PR C 2
N12' N 0.5387(15) 0.7480(4) 0.8880(4) 0.0365(19) Uani 0.506(5) 1 d PDU C 2
N11' N 0.7735(13) 0.7484(4) 0.8865(3) 0.0420(18) Uani 0.506(5) 1 d PDU C 2
N10' N 0.8650(14) 0.6873(4) 0.9161(3) 0.0460(18) Uani 0.506(5) 1 d PDU C 2
C55 C 0.3672(8) 0.8003(2) 0.79399(17) 0.0350(10) Uani 1 1 d . C .
C56 C 0.5566(9) 0.7725(2) 0.76336(18) 0.0457(12) Uani 1 1 d . . .
H56 H 0.7048 0.7556 0.7820 0.055 Uiso 1 1 calc R C .
C57 C 0.5345(9) 0.7689(2) 0.70620(19) 0.0478(12) Uani 1 1 d . C .
H57 H 0.6659 0.7488 0.6862 0.057 Uiso 1 1 calc R . .
C58 C 0.3249(9) 0.7941(2) 0.67862(19) 0.0410(12) Uani 1 1 d . . .
H58 H 0.3113 0.7929 0.6391 0.049 Uiso 1 1 calc R C .
C59 C 0.1331(9) 0.8213(2) 0.7080(2) 0.0492(13) Uani 1 1 d . C .
H59 H -0.0142 0.8383 0.6889 0.059 Uiso 1 1 calc R . .
C60 C 0.1543(9) 0.8240(2) 0.76579(19) 0.0451(12) Uani 1 1 d . . .
H60 H 0.0203 0.8424 0.7860 0.054 Uiso 1 1 calc R C .


_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 C1 1.213(5) . ?
O2 C2 1.220(5) . ?
N1 C2 1.393(5) . ?
N1 C1 1.394(5) . ?
N1 C9 1.452(5) . ?
N2 N3 1.324(5) . ?
N2 C12 1.362(5) . ?
N3 N4 1.343(4) . ?
N4 C13 1.345(5) . ?
N4 C14 1.459(5) . ?
C1 C4 1.490(6) . ?
C2 C3 1.481(5) . ?
C3 C8 1.373(6) . ?
C3 C4 1.375(6) . ?
C4 C5 1.377(5) . ?
C5 C6 1.392(6) . ?
C6 C7 1.373(6) . ?
C7 C8 1.390(6) . ?
C9 C10 1.511(5) . ?
C10 C11 1.523(5) . ?
C11 C12 1.494(6) . ?
C12 C13 1.370(5) . ?
C14 C15 1.514(6) . ?
C15 C20 1.367(6) . ?
C15 C16 1.379(6) . ?
C16 C17 1.375(7) . ?
C17 C18 1.370(7) . ?
C18 C19 1.374(7) . ?
C19 C20 1.403(6) . ?
O3 C21 1.216(5) . ?
O4 C22 1.211(5) . ?
N5 C22 1.392(5) . ?
N5 C21 1.398(5) . ?
N5 C29 1.464(5) . ?
N6 N7 1.328(5) . ?
N6 C32 1.361(5) . ?
N7 N8 1.334(5) . ?
N8 C33 1.339(5) . ?
N8 C34 1.460(5) . ?
C21 C24 1.483(5) . ?
C22 C23 1.491(5) . ?
C23 C24 1.368(5) . ?
C23 C28 1.383(5) . ?
C24 C25 1.373(5) . ?
C25 C26 1.384(6) . ?
C26 C27 1.389(6) . ?
C27 C28 1.399(6) . ?
C29 C30 1.526(5) . ?
C30 C31 1.501(6) . ?
C31 C32 1.501(5) . ?
C32 C33 1.365(6) . ?
C34 C35 1.516(6) . ?
C35 C36 1.377(6) . ?
C35 C40 1.380(6) . ?
C36 C37 1.389(6) . ?
C37 C38 1.352(7) . ?
C38 C39 1.374(7) . ?
C39 C40 1.415(7) . ?
O5 C41 1.222(5) . ?
O6 C42 1.204(5) . ?
N9 C41 1.372(6) . ?
N9 C42 1.398(5) . ?
N9 C49 1.456(5) . ?
C41 C44 1.489(6) . ?
C42 C43 1.499(6) . ?
C43 C48 1.376(5) . ?
C43 C44 1.376(6) . ?
C44 C45 1.373(6) . ?
C45 C46 1.380(6) . ?
C46 C47 1.375(6) . ?
C47 C48 1.393(6) . ?
C49 C50 1.517(6) . ?
C50 C51 1.525(12) . ?
C50 C51' 1.526(11) . ?
C54 N12' 1.437(8) . ?
C54 N12 1.469(8) . ?
C54 C55 1.505(6) . ?
C51 C52 1.468(11) . ?
C52 C53 1.338(11) . ?
C52 N10 1.347(11) . ?
C53 N12 1.357(10) . ?
N12 N11 1.328(10) . ?
N11 N10 1.326(9) . ?
C51' C52' 1.475(11) . ?
C52' C53' 1.336(11) . ?
C52' N10' 1.358(10) . ?
C53' N12' 1.351(10) . ?
N12' N11' 1.321(10) . ?
N11' N10' 1.332(9) . ?
C55 C60 1.377(6) . ?
C55 C56 1.383(6) . ?
C56 C57 1.383(6) . ?
C57 C58 1.360(6) . ?
C58 C59 1.372(6) . ?
C59 C60 1.394(6) . ?

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 111.2(3) . . ?
C2 N1 C9 124.0(3) . . ?
C1 N1 C9 124.8(4) . . ?
N3 N2 C12 109.2(3) . . ?
N2 N3 N4 106.8(3) . . ?
N3 N4 C13 110.9(3) . . ?
N3 N4 C14 119.9(3) . . ?
C13 N4 C14 129.2(4) . . ?
O1 C1 N1 124.4(4) . . ?
O1 C1 C4 129.6(4) . . ?
N1 C1 C4 105.9(4) . . ?
O2 C2 N1 125.0(4) . . ?
O2 C2 C3 128.5(4) . . ?
N1 C2 C3 106.5(4) . . ?
C8 C3 C4 121.8(4) . . ?
C8 C3 C2 130.2(4) . . ?
C4 C3 C2 108.0(4) . . ?
C3 C4 C5 121.4(4) . . ?
C3 C4 C1 108.2(3) . . ?
C5 C4 C1 130.3(4) . . ?
C4 C5 C6 116.8(4) . . ?
C7 C6 C5 121.9(4) . . ?
C6 C7 C8 120.7(4) . . ?
C3 C8 C7 117.4(4) . . ?
N1 C9 C10 112.8(3) . . ?
C9 C10 C11 112.2(3) . . ?
C12 C11 C10 114.5(3) . . ?
N2 C12 C13 107.6(4) . . ?
N2 C12 C11 121.8(4) . . ?
C13 C12 C11 130.5(4) . . ?
N4 C13 C12 105.4(4) . . ?
N4 C14 C15 113.2(3) . . ?
C20 C15 C16 118.7(4) . . ?
C20 C15 C14 120.8(4) . . ?
C16 C15 C14 120.4(4) . . ?
C17 C16 C15 121.2(5) . . ?
C18 C17 C16 120.3(5) . . ?
C17 C18 C19 119.4(5) . . ?
C18 C19 C20 120.0(5) . . ?
C15 C20 C19 120.4(4) . . ?
C22 N5 C21 111.3(3) . . ?
C22 N5 C29 125.1(3) . . ?
C21 N5 C29 123.5(3) . . ?
N7 N6 C32 108.7(4) . . ?
N6 N7 N8 106.8(3) . . ?
N7 N8 C33 111.2(3) . . ?
N7 N8 C34 119.9(3) . . ?
C33 N8 C34 128.7(4) . . ?
O3 C21 N5 123.9(4) . . ?
O3 C21 C24 129.9(4) . . ?
N5 C21 C24 106.2(3) . . ?
O4 C22 N5 124.6(4) . . ?
O4 C22 C23 129.6(4) . . ?
N5 C22 C23 105.8(3) . . ?
C24 C23 C28 121.7(4) . . ?
C24 C23 C22 108.5(3) . . ?
C28 C23 C22 129.8(4) . . ?
C23 C24 C25 122.4(4) . . ?
C23 C24 C21 108.2(3) . . ?
C25 C24 C21 129.5(4) . . ?
C24 C25 C26 117.2(4) . . ?
C25 C26 C27 120.9(4) . . ?
C26 C27 C28 121.5(4) . . ?
C23 C28 C27 116.4(4) . . ?
N5 C29 C30 112.6(3) . . ?
C31 C30 C29 114.2(3) . . ?
C32 C31 C30 113.4(3) . . ?
N6 C32 C33 107.9(4) . . ?
N6 C32 C31 121.6(4) . . ?
C33 C32 C31 130.5(4) . . ?
N8 C33 C32 105.4(4) . . ?
N8 C34 C35 111.3(3) . . ?
C36 C35 C40 119.2(4) . . ?
C36 C35 C34 120.4(4) . . ?
C40 C35 C34 120.4(4) . . ?
C35 C36 C37 120.2(5) . . ?
C38 C37 C36 121.0(5) . . ?
C37 C38 C39 120.3(5) . . ?
C38 C39 C40 119.2(5) . . ?
C35 C40 C39 120.1(5) . . ?
C41 N9 C42 112.0(4) . . ?
C41 N9 C49 124.5(4) . . ?
C42 N9 C49 123.4(4) . . ?
O5 C41 N9 124.7(4) . . ?
O5 C41 C44 128.5(5) . . ?
N9 C41 C44 106.8(4) . . ?
O6 C42 N9 124.7(4) . . ?
O6 C42 C43 130.1(4) . . ?
N9 C42 C43 105.3(4) . . ?
C48 C43 C44 121.7(4) . . ?
C48 C43 C42 130.1(4) . . ?
C44 C43 C42 108.2(4) . . ?
C45 C44 C43 121.3(4) . . ?
C45 C44 C41 131.1(4) . . ?
C43 C44 C41 107.7(4) . . ?
C44 C45 C46 117.7(5) . . ?
C47 C46 C45 121.2(5) . . ?
C46 C47 C48 121.3(4) . . ?
C43 C48 C47 116.8(5) . . ?
N9 C49 C50 111.5(3) . . ?
C49 C50 C51 118.1(8) . . ?
C49 C50 C51' 106.5(8) . . ?
N12' C54 C55 113.5(6) . . ?
N12 C54 C55 112.0(5) . . ?
C52 C51 C50 110.0(9) . . ?
C53 C52 N10 108.9(8) . . ?
C53 C52 C51 135.1(11) . . ?
N10 C52 C51 115.9(10) . . ?
C52 C53 N12 105.5(8) . . ?
N11 N12 C53 109.8(7) . . ?
N11 N12 C54 118.8(7) . . ?
C53 N12 C54 131.3(7) . . ?
N10 N11 N12 107.4(7) . . ?
N11 N10 C52 108.3(7) . . ?
C52' C51' C50 117.7(9) . . ?
C53' C52' N10' 107.7(8) . . ?
C53' C52' C51' 136.5(11) . . ?
N10' C52' C51' 115.7(10) . . ?
C52' C53' N12' 105.8(8) . . ?
N11' N12' C53' 111.3(7) . . ?
N11' N12' C54 119.1(7) . . ?
C53' N12' C54 129.3(7) . . ?
N12' N11' N10' 105.9(7) . . ?
N11' N10' C52' 109.4(7) . . ?
C60 C55 C56 117.8(4) . . ?
C60 C55 C54 120.1(4) . . ?
C56 C55 C54 122.0(4) . . ?
C57 C56 C55 121.4(4) . . ?
C58 C57 C56 120.1(5) . . ?
C57 C58 C59 119.9(4) . . ?
C58 C59 C60 120.0(4) . . ?
C55 C60 C59 120.8(4) . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        24.71
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.219
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.056
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_Faouzi18bis
_database_code_depnum_ccdc_archive 'CCDC 1020812'
_audit_update_record             
;
2014-08-22 deposited with the CCDC.
2015-01-30 downloaded from the CCDC.
;

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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C20 H13 N O4'
_chemical_formula_sum            'C20 H13 N O4'
_chemical_formula_weight         331.31
_chemical_compound_source        'synthesis as described'

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

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.1728(2)
_cell_length_b                   8.0196(2)
_cell_length_c                   12.8455(4)
_cell_angle_alpha                84.142(2)
_cell_angle_beta                 89.687(2)
_cell_angle_gamma                87.901(2)
_cell_volume                     734.56(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    193(2)
_cell_measurement_reflns_used    4791
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      25.35
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.06
_exptl_crystal_density_diffrn    1.498
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             344
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2006)'
_exptl_absorpt_correction_T_min  0.9874
_exptl_absorpt_correction_T_max  0.9937

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

_diffrn_ambient_temperature      193(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_radiation_probe          x-ray
_diffrn_reflns_av_R_equivalents  0.0279
_diffrn_reflns_av_unetI/netI     0.0228
_diffrn_reflns_number            12101
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.55
_diffrn_reflns_theta_max         25.34
_diffrn_reflns_theta_full        25.34
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_reflns_number_total             2691
_reflns_number_gt                2196
_reflns_threshold_expression     >2sigma(I)

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

_computing_data_collection       'APEX2 (Bruker, 2006)'
_computing_cell_refinement       'APEX2 and SAINT (Bruker, 2006)'
_computing_data_reduction        'SAINT (Bruker, 2006)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

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

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

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

_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)+(0.0616P)²+0.1016P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2691
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0478
_refine_ls_R_factor_gt           0.0379
_refine_ls_wR_factor_ref         0.1044
_refine_ls_wR_factor_gt          0.0976
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.161
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.058

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

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.32601(18) 0.26330(16) 0.89055(11) 0.0251(3) Uani 1 1 d . . .
C2 C 0.22412(18) 0.55057(16) 0.81715(11) 0.0241(3) Uani 1 1 d . . .
C3 C 0.20960(18) 0.60045(16) 0.92484(10) 0.0239(3) Uani 1 1 d . . .
C4 C 0.15643(19) 0.76259(17) 0.94018(11) 0.0280(3) Uani 1 1 d . . .
H4 H 0.1249 0.841 0.8819 0.034 Uiso 1 1 calc R . .
C5 C 0.1485(2) 0.81270(18) 1.04160(12) 0.0317(3) Uani 1 1 d . . .
H5 H 0.112 0.9251 1.0514 0.038 Uiso 1 1 calc R . .
C6 C 0.1928(2) 0.70179(19) 1.12659(12) 0.0313(3) Uani 1 1 d . . .
H6 H 0.1864 0.7381 1.1947 0.038 Uiso 1 1 calc R . .
C7 C 0.24785(18) 0.53363(17) 1.11447(11) 0.0265(3) Uani 1 1 d . . .
C8 C 0.2982(2) 0.41385(19) 1.19974(11) 0.0324(4) Uani 1 1 d . . .
H8 H 0.2923 0.4453 1.269 0.039 Uiso 1 1 calc R . .
C9 C 0.3551(2) 0.25378(19) 1.18348(11) 0.0328(4) Uani 1 1 d . . .
H9 H 0.3891 0.1755 1.2414 0.039 Uiso 1 1 calc R . .
C10 C 0.36368(19) 0.20449(18) 1.08149(11) 0.0293(3) Uani 1 1 d . . .
H10 H 0.4038 0.0933 1.0708 0.035 Uiso 1 1 calc R . .
C11 C 0.31419(18) 0.31657(16) 0.99723(11) 0.0246(3) Uani 1 1 d . . .
C12 C 0.25619(17) 0.48307(16) 1.01152(10) 0.0233(3) Uani 1 1 d . . .
C13 C 0.3114(2) 0.33409(18) 0.70022(11) 0.0287(3) Uani 1 1 d . . .
H13A H 0.4182 0.2523 0.7003 0.034 Uiso 1 1 calc R . .
H13B H 0.3419 0.4335 0.6518 0.034 Uiso 1 1 calc R . .
C14 C 0.14003(19) 0.25636(17) 0.66083(10) 0.0263(3) Uani 1 1 d . . .
C15 C 0.1211(2) 0.08339(18) 0.67424(11) 0.0308(3) Uani 1 1 d . . .
H15 H 0.2191 0.0146 0.707 0.037 Uiso 1 1 calc R . .
C16 C -0.0376(2) 0.00788(18) 0.64102(11) 0.0344(4) Uani 1 1 d . . .
H16 H -0.0507 -0.1101 0.6512 0.041 Uiso 1 1 calc R . .
C17 C -0.1734(2) 0.11273(18) 0.59307(11) 0.0304(3) Uani 1 1 d . . .
C18 C -0.1554(2) 0.28473(18) 0.57796(10) 0.0281(3) Uani 1 1 d . . .
C19 C -0.00149(19) 0.36071(17) 0.61119(10) 0.0272(3) Uani 1 1 d . . .
H19 H 0.009 0.479 0.6011 0.033 Uiso 1 1 calc R . .
C20 C -0.4090(2) 0.2219(2) 0.49392(12) 0.0375(4) Uani 1 1 d . . .
H20A H -0.5456 0.2387 0.5018 0.045 Uiso 1 1 calc R . .
H20B H -0.3806 0.2137 0.4191 0.045 Uiso 1 1 calc R . .
N1 N 0.28583(15) 0.38565(13) 0.80724(9) 0.0246(3) Uani 1 1 d . . .
O1 O 0.36979(15) 0.12082(12) 0.87345(8) 0.0365(3) Uani 1 1 d . . .
O2 O 0.18638(15) 0.64660(12) 0.73980(8) 0.0343(3) Uani 1 1 d . . .
O3 O -0.34481(15) 0.07254(13) 0.55591(8) 0.0400(3) Uani 1 1 d . . .
O4 O -0.31389(14) 0.35936(13) 0.53051(8) 0.0356(3) Uani 1 1 d . . .



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

_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
C1 O1 1.2151(16) . ?
C1 N1 1.3998(17) . ?
C1 C11 1.478(2) . ?
C2 O2 1.2186(16) . ?
C2 N1 1.3972(17) . ?
C2 C3 1.4808(19) . ?
C3 C4 1.3749(19) . ?
C3 C12 1.4159(18) . ?
C4 C5 1.402(2) . ?
C4 H4 0.95 . ?
C5 C6 1.367(2) . ?
C5 H5 0.95 . ?
C6 C7 1.415(2) . ?
C6 H6 0.95 . ?
C7 C8 1.420(2) . ?
C7 C12 1.4226(19) . ?
C8 C9 1.369(2) . ?
C8 H8 0.95 . ?
C9 C10 1.407(2) . ?
C9 H9 0.95 . ?
C10 C11 1.3740(19) . ?
C10 H10 0.95 . ?
C11 C12 1.4136(19) . ?
C13 N1 1.4840(17) . ?
C13 C14 1.511(2) . ?
C13 H13A 0.99 . ?
C13 H13B 0.99 . ?
C14 C15 1.392(2) . ?
C14 C19 1.405(2) . ?
C15 C16 1.398(2) . ?
C15 H15 0.95 . ?
C16 C17 1.370(2) . ?
C16 H16 0.95 . ?
C17 O3 1.3821(18) . ?
C17 C18 1.384(2) . ?
C18 C19 1.371(2) . ?
C18 O4 1.3806(17) . ?
C19 H19 0.95 . ?
C20 O3 1.4319(19) . ?
C20 O4 1.4372(19) . ?
C20 H20A 0.99 . ?
C20 H20B 0.99 . ?

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
O1 C1 N1 120.06(13) . . ?
O1 C1 C11 122.86(12) . . ?
N1 C1 C11 117.08(11) . . ?
O2 C2 N1 120.51(12) . . ?
O2 C2 C3 122.83(12) . . ?
N1 C2 C3 116.66(11) . . ?
C4 C3 C12 120.10(13) . . ?
C4 C3 C2 119.76(12) . . ?
C12 C3 C2 120.11(12) . . ?
C3 C4 C5 120.23(13) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C6 C5 C4 120.81(13) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C5 C6 C7 120.87(14) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 H6 119.6 . . ?
C6 C7 C8 123.27(13) . . ?
C6 C7 C12 118.26(13) . . ?
C8 C7 C12 118.46(13) . . ?
C9 C8 C7 120.94(14) . . ?
C9 C8 H8 119.5 . . ?
C7 C8 H8 119.5 . . ?
C8 C9 C10 120.39(13) . . ?
C8 C9 H9 119.8 . . ?
C10 C9 H9 119.8 . . ?
C11 C10 C9 120.25(13) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C10 C11 C12 120.63(13) . . ?
C10 C11 C1 119.55(12) . . ?
C12 C11 C1 119.81(12) . . ?
C11 C12 C3 120.94(13) . . ?
C11 C12 C7 119.32(12) . . ?
C3 C12 C7 119.73(12) . . ?
N1 C13 C14 112.55(11) . . ?
N1 C13 H13A 109.1 . . ?
C14 C13 H13A 109.1 . . ?
N1 C13 H13B 109.1 . . ?
C14 C13 H13B 109.1 . . ?
H13A C13 H13B 107.8 . . ?
C15 C14 C19 120.12(13) . . ?
C15 C14 C13 120.58(13) . . ?
C19 C14 C13 119.30(12) . . ?
C14 C15 C16 122.00(14) . . ?
C14 C15 H15 119 . . ?
C16 C15 H15 119 . . ?
C17 C16 C15 116.58(13) . . ?
C17 C16 H16 121.7 . . ?
C15 C16 H16 121.7 . . ?
C16 C17 O3 128.56(13) . . ?
C16 C17 C18 122.04(14) . . ?
O3 C17 C18 109.37(13) . . ?
C19 C18 O4 128.18(13) . . ?
C19 C18 C17 122.03(13) . . ?
O4 C18 C17 109.73(13) . . ?
C18 C19 C14 117.22(13) . . ?
C18 C19 H19 121.4 . . ?
C14 C19 H19 121.4 . . ?
O3 C20 O4 107.15(11) . . ?
O3 C20 H20A 110.3 . . ?
O4 C20 H20A 110.3 . . ?
O3 C20 H20B 110.3 . . ?
O4 C20 H20B 110.3 . . ?
H20A C20 H20B 108.5 . . ?
C2 N1 C1 125.29(11) . . ?
C2 N1 C13 118.05(11) . . ?
C1 N1 C13 116.66(11) . . ?
C17 O3 C20 104.22(11) . . ?
C18 O4 C20 103.97(11) . . ?


#===END
