# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 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/. 
# 
# Audit and citation data items have may 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_added_by_encifer
_database_code_depnum_ccdc_archive 'CCDC 1023999'
_audit_update_record             
;
2014-09-12 deposited with the CCDC.
2014-11-26 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H12 N2 O3'
_chemical_formula_weight         256.26

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/c

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

_cell_length_a                   4.822(2)
_cell_length_b                   22.257(10)
_cell_length_c                   11.408(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.364(4)
_cell_angle_gamma                90.00
_cell_volume                     1222.3(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3711
_cell_measurement_theta_min      1.8
_cell_measurement_theta_max      33.7

_exptl_crystal_description       needle
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             528
_exptl_absorpt_coefficient_mu    0.1
_exptl_absorpt_correction_type   multi-scan
# Example: '(North et al., 1968)'
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_absorpt_correction_T_min  0.9740
_exptl_absorpt_correction_T_max  0.9875


_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       
;
XtaLABmini: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  
;
Rigaku Mercury375R (2x2 bin mode)
;
_diffrn_detector_area_resol_mean 13.6612
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11349
_diffrn_reflns_av_R_equivalents  0.0935
_diffrn_reflns_av_sigmaI/netI    0.0514
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.83
_diffrn_reflns_theta_max         26.00
_reflns_number_total             2387
_reflns_number_gt                2115
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       
;
CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009)
;
_computing_structure_solution    'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(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)+(0.1395P)²+0.6654P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2387
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0614
_refine_ls_R_factor_gt           0.0527
_refine_ls_wR_factor_ref         0.1799
_refine_ls_wR_factor_gt          0.1596
_refine_ls_goodness_of_fit_ref   0.872
_refine_ls_restrained_S_all      0.872
_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
O3 O 0.0936(3) 0.59919(6) -0.00189(13) 0.0310(4) Uani 1 1 d . . .
C002 C 0.3329(4) 0.60081(8) -0.03487(16) 0.0231(4) Uani 1 1 d . . .
C003 C 0.4190(4) 0.55922(8) -0.13030(15) 0.0224(4) Uani 1 1 d . . .
N1 N 0.5245(3) 0.63922(7) 0.01011(13) 0.0240(4) Uani 1 1 d . . .
H1 H 0.6924 0.6398 -0.0162 0.029 Uiso 1 1 calc R . .
C005 C 0.5489(4) 0.48164(8) -0.30584(16) 0.0270(4) Uani 1 1 d . . .
C006 C 0.2838(4) 0.50405(8) -0.14234(17) 0.0260(4) Uani 1 1 d . . .
H006 H 0.1460 0.4935 -0.0898 0.031 Uiso 1 1 calc R . .
C007 C 0.6182(4) 0.57531(8) -0.20787(16) 0.0254(4) Uani 1 1 d . . .
H007 H 0.7094 0.6130 -0.1998 0.031 Uiso 1 1 calc R . .
C008 C 0.4509(4) 0.68036(8) 0.10404(17) 0.0269(4) Uani 1 1 d . . .
H00A H 0.4149 0.6569 0.1752 0.032 Uiso 1 1 calc R . .
H00B H 0.2783 0.7021 0.0792 0.032 Uiso 1 1 calc R . .
N2 N 0.6231(4) 0.43951(8) -0.39890(15) 0.0362(4) Uani 1 1 d . . .
C010 C 0.6790(4) 0.72514(8) 0.13302(16) 0.0248(4) Uani 1 1 d . . .
C011 C 0.6843(4) 0.53625(9) -0.29735(16) 0.0275(4) Uani 1 1 d . . .
H011 H 0.8192 0.5469 -0.3512 0.033 Uiso 1 1 calc R . .
C012 C 0.8328(4) 0.72295(10) 0.23975(18) 0.0335(5) Uani 1 1 d . . .
H012 H 0.7979 0.6921 0.2945 0.040 Uiso 1 1 calc R . .
C013 C 0.3490(4) 0.46449(8) -0.23053(17) 0.0287(4) Uani 1 1 d . . .
H013 H 0.2588 0.4267 -0.2389 0.034 Uiso 1 1 calc R . .
O1 O 0.7856(4) 0.45605(9) -0.46923(16) 0.0557(5) Uani 1 1 d . . .
C015 C 0.7328(4) 0.77079(9) 0.05453(18) 0.0331(5) Uani 1 1 d . . .
H015 H 0.6261 0.7734 -0.0180 0.040 Uiso 1 1 calc R . .
O2 O 0.5149(5) 0.39008(8) -0.40188(18) 0.0698(7) Uani 1 1 d . . .
C017 C 1.0361(5) 0.76524(12) 0.2671(2) 0.0451(6) Uani 1 1 d . . .
H017 H 1.1384 0.7637 0.3408 0.054 Uiso 1 1 calc R . .
C018 C 1.0909(5) 0.80975(11) 0.1874(2) 0.0472(7) Uani 1 1 d . . .
H018 H 1.2323 0.8385 0.2058 0.057 Uiso 1 1 calc R . .
C019 C 0.9392(5) 0.81240(10) 0.0806(2) 0.0435(6) Uani 1 1 d . . .
H019 H 0.9774 0.8428 0.0253 0.052 Uiso 1 1 calc R . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O3 C002 1.235(2) . ?
C002 N1 1.339(2) . ?
C002 C003 1.506(3) . ?
C003 C007 1.391(3) . ?
C003 C006 1.393(3) . ?
N1 C008 1.469(2) . ?
N1 H1 0.8800 . ?
C005 C013 1.382(3) . ?
C005 C011 1.381(3) . ?
C005 N2 1.476(2) . ?
C006 C013 1.387(3) . ?
C006 H006 0.9500 . ?
C007 C011 1.392(3) . ?
C007 H007 0.9500 . ?
C008 C010 1.506(3) . ?
C008 H00A 0.9900 . ?
C008 H00B 0.9900 . ?
N2 O2 1.218(3) . ?
N2 O1 1.211(2) . ?
C010 C012 1.389(3) . ?
C010 C015 1.389(3) . ?
C011 H011 0.9500 . ?
C012 C017 1.381(3) . ?
C012 H012 0.9500 . ?
C013 H013 0.9500 . ?
C015 C019 1.379(3) . ?
C015 H015 0.9500 . ?
C017 C018 1.381(4) . ?
C017 H017 0.9500 . ?
C018 C019 1.385(4) . ?
C018 H018 0.9500 . ?
C019 H019 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 C002 N1 122.56(17) . . ?
O3 C002 C003 120.28(16) . . ?
N1 C002 C003 117.16(16) . . ?
C007 C003 C006 120.06(17) . . ?
C007 C003 C002 122.12(16) . . ?
C006 C003 C002 117.77(16) . . ?
C002 N1 C008 119.14(15) . . ?
C002 N1 H1 120.4 . . ?
C008 N1 H1 120.4 . . ?
C013 C005 C011 122.96(17) . . ?
C013 C005 N2 118.62(17) . . ?
C011 C005 N2 118.42(17) . . ?
C013 C006 C003 120.42(17) . . ?
C013 C006 H006 119.8 . . ?
C003 C006 H006 119.8 . . ?
C003 C007 C011 120.16(17) . . ?
C003 C007 H007 119.9 . . ?
C011 C007 H007 119.9 . . ?
N1 C008 C010 111.60(14) . . ?
N1 C008 H00A 109.3 . . ?
C010 C008 H00A 109.3 . . ?
N1 C008 H00B 109.3 . . ?
C010 C008 H00B 109.3 . . ?
H00A C008 H00B 108.0 . . ?
O2 N2 O1 123.31(18) . . ?
O2 N2 C005 118.19(18) . . ?
O1 N2 C005 118.49(18) . . ?
C012 C010 C015 118.72(18) . . ?
C012 C010 C008 120.97(17) . . ?
C015 C010 C008 120.27(18) . . ?
C005 C011 C007 118.26(17) . . ?
C005 C011 H011 120.9 . . ?
C007 C011 H011 120.9 . . ?
C010 C012 C017 120.6(2) . . ?
C010 C012 H012 119.7 . . ?
C017 C012 H012 119.7 . . ?
C005 C013 C006 118.14(17) . . ?
C005 C013 H013 120.9 . . ?
C006 C013 H013 120.9 . . ?
C010 C015 C019 120.8(2) . . ?
C010 C015 H015 119.6 . . ?
C019 C015 H015 119.6 . . ?
C018 C017 C012 120.1(2) . . ?
C018 C017 H017 120.0 . . ?
C012 C017 H017 120.0 . . ?
C017 C018 C019 119.9(2) . . ?
C017 C018 H018 120.1 . . ?
C019 C018 H018 120.1 . . ?
C015 C019 C018 119.9(2) . . ?
C015 C019 H019 120.1 . . ?
C018 C019 H019 120.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O3 C002 C003 C007 148.85(18) . . . . ?
N1 C002 C003 C007 -30.4(2) . . . . ?
O3 C002 C003 C006 -28.6(2) . . . . ?
N1 C002 C003 C006 152.19(17) . . . . ?
O3 C002 N1 C008 1.3(3) . . . . ?
C003 C002 N1 C008 -179.53(15) . . . . ?
C007 C003 C006 C013 0.8(3) . . . . ?
C002 C003 C006 C013 178.34(16) . . . . ?
C006 C003 C007 C011 -0.4(3) . . . . ?
C002 C003 C007 C011 -177.74(17) . . . . ?
C002 N1 C008 C010 -172.90(16) . . . . ?
C013 C005 N2 O2 -3.6(3) . . . . ?
C011 C005 N2 O2 175.8(2) . . . . ?
C013 C005 N2 O1 175.5(2) . . . . ?
C011 C005 N2 O1 -5.1(3) . . . . ?
N1 C008 C010 C012 -111.23(19) . . . . ?
N1 C008 C010 C015 70.9(2) . . . . ?
C013 C005 C011 C007 0.8(3) . . . . ?
N2 C005 C011 C007 -178.59(16) . . . . ?
C003 C007 C011 C005 -0.4(3) . . . . ?
C015 C010 C012 C017 -0.2(3) . . . . ?
C008 C010 C012 C017 -178.10(18) . . . . ?
C011 C005 C013 C006 -0.3(3) . . . . ?
N2 C005 C013 C006 179.06(17) . . . . ?
C003 C006 C013 C005 -0.5(3) . . . . ?
C012 C010 C015 C019 1.5(3) . . . . ?
C008 C010 C015 C019 179.37(18) . . . . ?
C010 C012 C017 C018 -0.9(3) . . . . ?
C012 C017 C018 C019 0.8(3) . . . . ?
C010 C015 C019 C018 -1.6(3) . . . . ?
C017 C018 C019 C015 0.4(3) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.262
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.074
####################################################################### 
# 
# 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/. 
# 
# Audit and citation data items have may 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_added_by_encifer
_database_code_depnum_ccdc_archive 'CCDC 1024000'
_audit_update_record             
;
2014-09-12 deposited with the CCDC.
2014-11-26 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H7 N O4'
_chemical_formula_weight         181.15

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                   7.463
_cell_length_b                   7.747
_cell_length_c                   15.435
_cell_angle_alpha                94.52
_cell_angle_beta                 97.04
_cell_angle_gamma                117.68
_cell_volume                     774.8
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    1926
_cell_measurement_theta_min      2.7
_cell_measurement_theta_max      33.8

_exptl_crystal_description       Block
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.553
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             330
_exptl_absorpt_coefficient_mu    0.124
_exptl_absorpt_correction_type   multi-scan
# Example: '(North et al., 1968)'
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_absorpt_correction_T_min  0.9744
_exptl_absorpt_correction_T_max  0.9756


_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       
;
XtaLABmini: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  
;
Rigaku Mercury375R (2x2 bin mode)
;
_diffrn_detector_area_resol_mean 13.6612
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6992
_diffrn_reflns_av_R_equivalents  0.0597
_diffrn_reflns_av_sigmaI/netI    0.0576
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.35
_diffrn_reflns_theta_max         26.00
_reflns_number_total             3029
_reflns_number_gt                2216
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       
;
CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009)
;
_computing_structure_solution    'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(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)+(0.1997P)²+0.2384P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3029
_refine_ls_number_parameters     237
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0997
_refine_ls_R_factor_gt           0.0755
_refine_ls_wR_factor_ref         0.2758
_refine_ls_wR_factor_gt          0.2310
_refine_ls_goodness_of_fit_ref   0.974
_refine_ls_restrained_S_all      0.974
_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
C1 C 0.7756(4) 1.3005(4) 0.33041(18) 0.0277(7) Uani 1 1 d . . .
C30 C 0.7806(5) 0.7985(4) 0.34246(19) 0.0283(7) Uani 1 1 d . . .
C31 C 0.7010(4) 0.8055(4) 0.25728(18) 0.0264(6) Uani 1 1 d . . .
H31 H 0.5674 0.7934 0.2452 0.032 Uiso 1 1 calc R . .
N2 N 1.1294(4) 1.3731(4) 0.13047(17) 0.0303(6) Uani 1 1 d . . .
C34 C 0.6926(4) 1.3032(4) 0.24492(19) 0.0276(6) Uani 1 1 d . . .
H34 H 0.5588 1.2910 0.2338 0.033 Uiso 1 1 calc R . .
N1 N 1.1434(4) 0.8827(4) 0.14687(16) 0.0287(6) Uani 1 1 d . . .
C4 C 0.9971(4) 1.3450(4) 0.19751(18) 0.0259(6) Uani 1 1 d . . .
O9 O 0.4849(3) 1.2805(4) 0.38481(14) 0.0417(6) Uani 1 1 d . . .
H9 H 0.4321 1.2685 0.4305 0.062 Uiso 1 1 calc R . .
O1 O 0.7275(4) 1.2646(4) 0.47785(14) 0.0444(7) Uani 1 1 d . . .
C32 C 0.8135(4) 0.8298(4) 0.18916(19) 0.0267(6) Uani 1 1 d . . .
C5 C 0.7994(4) 1.3231(4) 0.17523(18) 0.0267(6) Uani 1 1 d . . .
C40 C 1.0886(4) 0.8360(4) 0.2963(2) 0.0300(7) Uani 1 1 d . . .
H40 H 1.2207 0.8445 0.3083 0.036 Uiso 1 1 calc R . .
O3 O 0.4881(4) 0.7776(4) 0.39645(15) 0.0425(7) Uani 1 1 d . . .
H3 H 0.4340 0.7634 0.4418 0.064 Uiso 1 1 calc R . .
C6 C 1.0076(4) 0.8472(4) 0.21238(19) 0.0264(6) Uani 1 1 d . . .
C7 C 0.6560(5) 0.7747(5) 0.41325(19) 0.0310(7) Uani 1 1 d . . .
O8 O 0.7260(4) 0.7529(4) 0.48815(14) 0.0429(7) Uani 1 1 d . . .
C35 C 0.6547(4) 1.2800(5) 0.40187(19) 0.0308(7) Uani 1 1 d . . .
C9 C 1.0830(5) 1.3428(5) 0.2824(2) 0.0317(7) Uani 1 1 d . . .
H9A H 1.2179 1.3581 0.2943 0.038 Uiso 1 1 calc R . .
C33 C 0.9699(5) 1.3180(5) 0.3490(2) 0.0304(7) Uani 1 1 d . . .
H33 H 1.0248 1.3130 0.4071 0.036 Uiso 1 1 calc R . .
C10 C 0.9725(5) 0.8119(5) 0.3623(2) 0.0315(7) Uani 1 1 d . . .
H10 H 1.0243 0.8047 0.4205 0.038 Uiso 1 1 calc R . .
C11 C 0.7179(4) 0.8281(5) 0.09715(18) 0.0296(7) Uani 1 1 d . . .
H11A H 0.7845 0.9616 0.0820 0.044 Uiso 1 1 calc R . .
H11B H 0.5707 0.7832 0.0944 0.044 Uiso 1 1 calc R . .
H11C H 0.7362 0.7385 0.0551 0.044 Uiso 1 1 calc R . .
O5 O 1.0500(4) 1.3325(4) 0.05290(15) 0.0419(6) Uani 1 1 d . . .
O4 O 1.3122(3) 1.4330(3) 0.15627(16) 0.0410(6) Uani 1 1 d . . .
C14 C 0.6977(5) 1.3244(5) 0.0855(2) 0.0353(7) Uani 1 1 d . . .
H14A H 0.6714 1.2074 0.0453 0.053 Uiso 1 1 calc R . .
H14B H 0.7881 1.4435 0.0627 0.053 Uiso 1 1 calc R . .
H14C H 0.5672 1.3232 0.0897 0.053 Uiso 1 1 calc R . .
O7 O 1.2398(4) 0.7905(4) 0.14522(16) 0.0450(7) Uani 1 1 d . . .
O6 O 1.1592(4) 1.0050(3) 0.09998(16) 0.0411(6) Uani 1 1 d . . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C33 1.383(4) . ?
C1 C34 1.393(4) . ?
C1 C35 1.481(4) . ?
C30 C10 1.380(4) . ?
C30 C31 1.391(4) . ?
C30 C7 1.488(4) . ?
C31 C32 1.395(4) . ?
C31 H31 0.9500 . ?
N2 O5 1.215(3) . ?
N2 O4 1.219(3) . ?
N2 C4 1.476(4) . ?
C34 C5 1.393(4) . ?
C34 H34 0.9500 . ?
N1 O6 1.209(3) . ?
N1 O7 1.227(3) . ?
N1 C6 1.470(4) . ?
C4 C9 1.392(4) . ?
C4 C5 1.399(4) . ?
O9 C35 1.264(4) . ?
O9 H9 0.8400 . ?
O1 C35 1.269(4) . ?
C32 C6 1.389(4) . ?
C32 C11 1.505(4) . ?
C5 C14 1.499(4) . ?
C40 C10 1.385(4) . ?
C40 C6 1.388(4) . ?
C40 H40 0.9500 . ?
O3 C7 1.260(4) . ?
O3 H3 0.8400 . ?
C7 O8 1.266(4) . ?
C9 C33 1.378(4) . ?
C9 H9A 0.9500 . ?
C33 H33 0.9500 . ?
C10 H10 0.9500 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C33 C1 C34 120.6(3) . . ?
C33 C1 C35 119.9(3) . . ?
C34 C1 C35 119.6(3) . . ?
C10 C30 C31 121.1(3) . . ?
C10 C30 C7 119.5(3) . . ?
C31 C30 C7 119.4(3) . . ?
C30 C31 C32 121.3(3) . . ?
C30 C31 H31 119.4 . . ?
C32 C31 H31 119.4 . . ?
O5 N2 O4 123.7(2) . . ?
O5 N2 C4 118.5(2) . . ?
O4 N2 C4 117.9(2) . . ?
C5 C34 C1 122.1(3) . . ?
C5 C34 H34 119.0 . . ?
C1 C34 H34 119.0 . . ?
O6 N1 O7 123.8(2) . . ?
O6 N1 C6 118.4(2) . . ?
O7 N1 C6 117.7(2) . . ?
C9 C4 C5 123.5(3) . . ?
C9 C4 N2 115.5(2) . . ?
C5 C4 N2 121.0(2) . . ?
C35 O9 H9 109.5 . . ?
C6 C32 C31 115.7(3) . . ?
C6 C32 C11 124.8(3) . . ?
C31 C32 C11 119.5(3) . . ?
C34 C5 C4 115.4(3) . . ?
C34 C5 C14 118.3(3) . . ?
C4 C5 C14 126.3(3) . . ?
C10 C40 C6 118.5(3) . . ?
C10 C40 H40 120.8 . . ?
C6 C40 H40 120.8 . . ?
C7 O3 H3 109.5 . . ?
C40 C6 C32 124.1(3) . . ?
C40 C6 N1 115.5(2) . . ?
C32 C6 N1 120.4(2) . . ?
O3 C7 O8 123.2(3) . . ?
O3 C7 C30 119.2(3) . . ?
O8 C7 C30 117.6(3) . . ?
O9 C35 O1 122.9(3) . . ?
O9 C35 C1 118.7(3) . . ?
O1 C35 C1 118.4(2) . . ?
C33 C9 C4 119.2(3) . . ?
C33 C9 H9A 120.4 . . ?
C4 C9 H9A 120.4 . . ?
C9 C33 C1 119.2(3) . . ?
C9 C33 H33 120.4 . . ?
C1 C33 H33 120.4 . . ?
C40 C10 C30 119.2(3) . . ?
C40 C10 H10 120.4 . . ?
C30 C10 H10 120.4 . . ?
C32 C11 H11A 109.5 . . ?
C32 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C32 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C5 C14 H14A 109.5 . . ?
C5 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C5 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C10 C30 C31 C32 -1.2(5) . . . . ?
C7 C30 C31 C32 179.3(3) . . . . ?
C33 C1 C34 C5 0.0(5) . . . . ?
C35 C1 C34 C5 179.7(3) . . . . ?
O5 N2 C4 C9 163.6(3) . . . . ?
O4 N2 C4 C9 -15.2(4) . . . . ?
O5 N2 C4 C5 -16.6(4) . . . . ?
O4 N2 C4 C5 164.6(3) . . . . ?
C30 C31 C32 C6 -0.3(4) . . . . ?
C30 C31 C32 C11 177.5(3) . . . . ?
C1 C34 C5 C4 -1.5(4) . . . . ?
C1 C34 C5 C14 -180.0(3) . . . . ?
C9 C4 C5 C34 1.5(4) . . . . ?
N2 C4 C5 C34 -178.3(2) . . . . ?
C9 C4 C5 C14 179.9(3) . . . . ?
N2 C4 C5 C14 0.1(5) . . . . ?
C10 C40 C6 C32 -2.1(5) . . . . ?
C10 C40 C6 N1 177.1(3) . . . . ?
C31 C32 C6 C40 2.0(5) . . . . ?
C11 C32 C6 C40 -175.7(3) . . . . ?
C31 C32 C6 N1 -177.2(2) . . . . ?
C11 C32 C6 N1 5.2(5) . . . . ?
O6 N1 C6 C40 -134.5(3) . . . . ?
O7 N1 C6 C40 43.0(4) . . . . ?
O6 N1 C6 C32 44.7(4) . . . . ?
O7 N1 C6 C32 -137.8(3) . . . . ?
C10 C30 C7 O3 174.7(3) . . . . ?
C31 C30 C7 O3 -5.8(5) . . . . ?
C10 C30 C7 O8 -5.1(5) . . . . ?
C31 C30 C7 O8 174.4(3) . . . . ?
C33 C1 C35 O9 174.3(3) . . . . ?
C34 C1 C35 O9 -5.3(5) . . . . ?
C33 C1 C35 O1 -5.1(5) . . . . ?
C34 C1 C35 O1 175.3(3) . . . . ?
C5 C4 C9 C33 -0.1(5) . . . . ?
N2 C4 C9 C33 179.7(3) . . . . ?
C4 C9 C33 C1 -1.5(5) . . . . ?
C34 C1 C33 C9 1.5(5) . . . . ?
C35 C1 C33 C9 -178.1(3) . . . . ?
C6 C40 C10 C30 0.5(5) . . . . ?
C31 C30 C10 C40 1.1(5) . . . . ?
C7 C30 C10 C40 -179.4(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.552
_refine_diff_density_min         -0.404
_refine_diff_density_rms         0.103
####################################################################### 
# 
# 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/. 
# 
# Audit and citation data items have may 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_added_by_encifer
_database_code_depnum_ccdc_archive 'CCDC 1024001'
_audit_update_record             
;
2014-09-12 deposited with the CCDC.
2014-11-26 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H15 N3 O4'
_chemical_formula_weight         289.2902

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c

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

_cell_length_a                   28.784(19)
_cell_length_b                   6.795(4)
_cell_length_c                   14.074(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.543(9)
_cell_angle_gamma                90.00
_cell_volume                     2744(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4681
_cell_measurement_theta_min      2.1
_cell_measurement_theta_max      33.9

_exptl_crystal_description       Block
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1216
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_type   multi-scan
# Example: '(North et al., 1968)'
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_absorpt_correction_T_min  0.9783
_exptl_absorpt_correction_T_max  0.9794


_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       
;
XtaLABmini: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  
;
Rigaku Mercury375R (2x2 bin mode)
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean 13.6612
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12169
_diffrn_reflns_av_R_equivalents  0.0681
_diffrn_reflns_av_sigmaI/netI    0.0389
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.42
_diffrn_reflns_theta_max         26.00
_reflns_number_total             2705
_reflns_number_gt                2488
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       
;
CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009)
;
_computing_structure_solution    'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(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)+(0.0932P)²+0.8153P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2705
_refine_ls_number_parameters     192
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0510
_refine_ls_R_factor_gt           0.0474
_refine_ls_wR_factor_ref         0.1479
_refine_ls_wR_factor_gt          0.1432
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_restrained_S_all      1.100
_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
C001 C 0.09855(4) 0.8209(2) 0.23016(9) 0.0243(3) Uani 1 1 d . . .
O4 O 0.14223(3) 0.53625(15) 0.27651(7) 0.0320(3) Uani 1 1 d . . .
O3 O 0.17079(3) 0.82994(16) 0.32469(8) 0.0358(3) Uani 1 1 d . . .
C004 C 0.02360(4) 0.7981(2) 0.14333(9) 0.0256(3) Uani 1 1 d . . .
C005 C 0.06174(4) 0.7060(2) 0.19090(9) 0.0247(3) Uani 1 1 d . . .
H005 H 0.0628 0.5667 0.1966 0.030 Uiso 1 1 calc R . .
N2 N -0.01513(4) 0.67606(19) 0.10162(8) 0.0311(3) Uani 1 1 d . . .
C007 C 0.14081(4) 0.7231(2) 0.28191(9) 0.0258(3) Uani 1 1 d . . .
C008 C 0.09597(5) 1.0248(2) 0.22038(10) 0.0318(3) Uani 1 1 d . . .
H008 H 0.1209 1.1043 0.2468 0.038 Uiso 1 1 calc R . .
O2 O -0.01268(4) 0.49707(18) 0.11157(10) 0.0488(3) Uani 1 1 d . . .
O1 O -0.04830(4) 0.7596(2) 0.05923(9) 0.0472(3) Uani 1 1 d . . .
C011 C 0.02039(5) 1.0006(2) 0.13350(10) 0.0329(3) Uani 1 1 d . . .
H011 H -0.0062 1.0603 0.1012 0.040 Uiso 1 1 calc R . .
C012 C 0.05733(6) 1.1132(2) 0.17234(11) 0.0391(4) Uani 1 1 d . . .
H012 H 0.0562 1.2523 0.1661 0.047 Uiso 1 1 calc R . .
C013 C 0.19099(4) 0.7720(2) 0.06875(8) 0.0238(3) Uani 1 1 d . . .
C014 C 0.20312(5) 0.9755(2) 0.06699(10) 0.0288(3) Uani 1 1 d . . .
H014 H 0.1819 1.0681 0.0373 0.035 Uiso 1 1 calc R . .
N1 N 0.27640(4) 0.91194(18) 0.15127(8) 0.0284(3) Uani 1 1 d . . .
H1 H 0.3034 0.9556 0.1765 0.034 Uiso 1 1 calc R . .
N3 N 0.15092(4) 0.70227(18) 0.02624(8) 0.0292(3) Uani 1 1 d . . .
C017 C 0.26586(5) 0.7194(2) 0.15562(9) 0.0277(3) Uani 1 1 d . . .
H017 H 0.2879 0.6319 0.1864 0.033 Uiso 1 1 calc R . .
C018 C 0.22446(5) 0.6460(2) 0.11718(9) 0.0275(3) Uani 1 1 d . . .
H018 H 0.2179 0.5096 0.1228 0.033 Uiso 1 1 calc R . .
C019 C 0.24522(5) 1.0375(2) 0.10790(10) 0.0307(3) Uani 1 1 d . . .
H019 H 0.2528 1.1735 0.1057 0.037 Uiso 1 1 calc R . .
C020 C 0.13941(5) 0.4938(2) 0.03089(11) 0.0371(4) Uani 1 1 d . . .
H02A H 0.1610 0.4177 -0.0050 0.056 Uiso 1 1 calc R . .
H02B H 0.1075 0.4728 0.0033 0.056 Uiso 1 1 calc R . .
H02C H 0.1420 0.4506 0.0975 0.056 Uiso 1 1 calc R . .
C021 C 0.11816(5) 0.8306(3) -0.02878(11) 0.0396(4) Uani 1 1 d . . .
H02D H 0.1016 0.9128 0.0148 0.059 Uiso 1 1 calc R . .
H02E H 0.0956 0.7503 -0.0676 0.059 Uiso 1 1 calc R . .
H02F H 0.1352 0.9150 -0.0705 0.059 Uiso 1 1 calc R . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C001 C005 1.3944(19) . ?
C001 C008 1.393(2) . ?
C001 C007 1.5202(18) . ?
O4 C007 1.2728(19) . ?
O3 C007 1.2457(17) . ?
C004 C011 1.385(2) . ?
C004 C005 1.3887(18) . ?
C004 N2 1.4732(18) . ?
C005 H005 0.9500 . ?
N2 O1 1.2247(16) . ?
N2 O2 1.2256(19) . ?
C008 C012 1.391(2) . ?
C008 H008 0.9500 . ?
C011 C012 1.387(2) . ?
C011 H011 0.9500 . ?
C012 H012 0.9500 . ?
C013 N3 1.3429(18) . ?
C013 C014 1.427(2) . ?
C013 C018 1.4220(19) . ?
C014 C019 1.366(2) . ?
C014 H014 0.9500 . ?
N1 C017 1.345(2) . ?
N1 C019 1.3490(19) . ?
N1 H1 0.8800 . ?
N3 C020 1.458(2) . ?
N3 C021 1.4609(19) . ?
C017 C018 1.363(2) . ?
C017 H017 0.9500 . ?
C018 H018 0.9500 . ?
C019 H019 0.9500 . ?
C020 H02A 0.9800 . ?
C020 H02B 0.9800 . ?
C020 H02C 0.9800 . ?
C021 H02D 0.9800 . ?
C021 H02E 0.9800 . ?
C021 H02F 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C005 C001 C008 118.98(12) . . ?
C005 C001 C007 119.95(13) . . ?
C008 C001 C007 121.07(12) . . ?
C011 C004 C005 122.63(12) . . ?
C011 C004 N2 118.48(12) . . ?
C005 C004 N2 118.89(13) . . ?
C004 C005 C001 119.07(13) . . ?
C004 C005 H005 120.5 . . ?
C001 C005 H005 120.5 . . ?
O1 N2 O2 123.46(12) . . ?
O1 N2 C004 117.99(13) . . ?
O2 N2 C004 118.55(12) . . ?
O3 C007 O4 125.86(12) . . ?
O3 C007 C001 118.31(13) . . ?
O4 C007 C001 115.83(11) . . ?
C012 C008 C001 120.76(13) . . ?
C012 C008 H008 119.6 . . ?
C001 C008 H008 119.6 . . ?
C004 C011 C012 117.76(13) . . ?
C004 C011 H011 121.1 . . ?
C012 C011 H011 121.1 . . ?
C011 C012 C008 120.79(14) . . ?
C011 C012 H012 119.6 . . ?
C008 C012 H012 119.6 . . ?
N3 C013 C014 122.47(12) . . ?
N3 C013 C018 121.77(13) . . ?
C014 C013 C018 115.75(12) . . ?
C019 C014 C013 120.10(13) . . ?
C019 C014 H014 120.0 . . ?
C013 C014 H014 119.9 . . ?
C017 N1 C019 119.42(12) . . ?
C017 N1 H1 120.3 . . ?
C019 N1 H1 120.3 . . ?
C013 N3 C020 120.88(12) . . ?
C013 N3 C021 121.40(13) . . ?
C020 N3 C021 117.69(12) . . ?
N1 C017 C018 122.07(12) . . ?
N1 C017 H017 119.0 . . ?
C018 C017 H017 119.0 . . ?
C017 C018 C013 120.49(13) . . ?
C017 C018 H018 119.8 . . ?
C013 C018 H018 119.8 . . ?
N1 C019 C014 122.13(13) . . ?
N1 C019 H019 118.9 . . ?
C014 C019 H019 118.9 . . ?
N3 C020 H02A 109.5 . . ?
N3 C020 H02B 109.5 . . ?
H02A C020 H02B 109.5 . . ?
N3 C020 H02C 109.5 . . ?
H02A C020 H02C 109.5 . . ?
H02B C020 H02C 109.5 . . ?
N3 C021 H02D 109.5 . . ?
N3 C021 H02E 109.5 . . ?
H02D C021 H02E 109.5 . . ?
N3 C021 H02F 109.5 . . ?
H02D C021 H02F 109.5 . . ?
H02E C021 H02F 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C011 C004 C005 C001 -0.31(19) . . . . ?
N2 C004 C005 C001 179.75(10) . . . . ?
C008 C001 C005 C004 -0.08(18) . . . . ?
C007 C001 C005 C004 -179.56(10) . . . . ?
C011 C004 N2 O1 0.67(18) . . . . ?
C005 C004 N2 O1 -179.39(12) . . . . ?
C011 C004 N2 O2 -178.85(13) . . . . ?
C005 C004 N2 O2 1.09(18) . . . . ?
C005 C001 C007 O3 -172.60(11) . . . . ?
C008 C001 C007 O3 7.94(18) . . . . ?
C005 C001 C007 O4 7.90(17) . . . . ?
C008 C001 C007 O4 -171.57(12) . . . . ?
C005 C001 C008 C012 0.1(2) . . . . ?
C007 C001 C008 C012 179.54(13) . . . . ?
C005 C004 C011 C012 0.7(2) . . . . ?
N2 C004 C011 C012 -179.38(13) . . . . ?
C004 C011 C012 C008 -0.7(2) . . . . ?
C001 C008 C012 C011 0.3(2) . . . . ?
N3 C013 C014 C019 -177.19(12) . . . . ?
C018 C013 C014 C019 1.77(18) . . . . ?
C014 C013 N3 C020 -179.01(12) . . . . ?
C018 C013 N3 C020 2.09(18) . . . . ?
C014 C013 N3 C021 3.08(19) . . . . ?
C018 C013 N3 C021 -175.83(12) . . . . ?
C019 N1 C017 C018 0.19(19) . . . . ?
N1 C017 C018 C013 1.33(19) . . . . ?
N3 C013 C018 C017 176.73(12) . . . . ?
C014 C013 C018 C017 -2.24(18) . . . . ?
C017 N1 C019 C014 -0.7(2) . . . . ?
C013 C014 C019 N1 -0.4(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.255
_refine_diff_density_min         -0.288
_refine_diff_density_rms         0.050
####################################################################### 
# 
# 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/. 
# 
# Audit and citation data items have may 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_datam
_database_code_depnum_ccdc_archive 'CCDC 1024002'
_audit_update_record             
;
2014-09-12 deposited with the CCDC.
2014-11-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H15 Cl O3'
_chemical_formula_sum            'C17 H15 Cl O3'
_chemical_formula_weight         302.74

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

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

_cell_length_a                   15.0137(18)
_cell_length_b                   5.7145(7)
_cell_length_c                   17.311(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.671(7)
_cell_angle_gamma                90.00
_cell_volume                     1430.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    173
_cell_measurement_reflns_used    11455
_cell_measurement_theta_min      3.1
_cell_measurement_theta_max      27.6

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.406
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             736
_exptl_absorpt_coefficient_mu    0.274
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      173
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       
;
XtaLABmini: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  
;
Rigaku Mercury375R (2x2 bin mode)
;
_diffrn_detector_area_resol_mean 13.6612
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            15259
_diffrn_reflns_av_R_equivalents  0.031
_diffrn_reflns_av_unetI/netI     0.043
_diffrn_reflns_av_sigmaI/netI    0.0214
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.19
_diffrn_reflns_theta_max         26.15
_reflns_number_total             2838
_reflns_number_gt                2609
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       
;
CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009)
;
_computing_structure_solution    'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(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)+(0.0405P)²+0.5273P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2838
_refine_ls_number_parameters     250
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0331
_refine_ls_R_factor_gt           0.0302
_refine_ls_wR_factor_ref         0.0814
_refine_ls_wR_factor_gt          0.0795
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_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
H5 H 0.0437(11) 0.210(3) 0.0598(10) 0.030(4) Uiso 1 1 d . . .
H6 H -0.1661(11) 0.534(3) 0.1812(9) 0.025(4) Uiso 1 1 d . . .
H7 H -0.3017(11) 0.555(3) 0.2195(9) 0.021(4) Uiso 1 1 d . . .
H8 H -0.2616(11) -0.050(3) 0.0505(9) 0.025(4) Uiso 1 1 d . . .
H9 H -0.4138(11) -0.149(3) -0.0227(10) 0.029(4) Uiso 1 1 d . . .
H10 H -0.4221(12) 0.458(3) 0.2780(11) 0.036(5) Uiso 1 1 d . . .
H11 H -0.4554(11) 0.612(3) 0.1981(10) 0.033(4) Uiso 1 1 d . . .
H12 H -0.5291(12) 0.442(3) 0.2228(9) 0.031(4) Uiso 1 1 d . . .
H13 H -0.3709(12) -0.350(3) 0.0422(10) 0.033(4) Uiso 1 1 d . . .
H14 H -0.4793(12) -0.313(3) 0.0141(10) 0.037(5) Uiso 1 1 d . . .
H15 H -0.0501(12) 0.515(3) 0.1334(10) 0.032(4) Uiso 1 1 d . . .
H1 H 0.2047(12) 0.994(3) 0.1921(10) 0.031(4) Uiso 1 1 d . . .
H2 H 0.0703(12) 0.766(3) 0.1612(9) 0.032(4) Uiso 1 1 d . . .
H3 H 0.1972(11) 0.287(3) 0.0555(10) 0.033(4) Uiso 1 1 d . . .
H4 H 0.3310(12) 0.518(3) 0.0850(9) 0.029(4) Uiso 1 1 d . . .
C1 C 0.27883(9) 0.7743(2) 0.14159(8) 0.0206(3) Uani 1 1 d . . .
C2 C 0.27768(9) 0.5661(2) 0.10047(8) 0.0237(3) Uani 1 1 d . . .
C3 C 0.19862(9) 0.4297(2) 0.08291(8) 0.0229(3) Uani 1 1 d . . .
C4 C 0.12045(9) 0.4985(2) 0.10572(7) 0.0198(3) Uani 1 1 d . . .
C5 C 0.12359(9) 0.7116(3) 0.14636(8) 0.0248(3) Uani 1 1 d . . .
C6 C 0.20236(10) 0.8486(3) 0.16496(8) 0.0251(3) Uani 1 1 d . . .
C7 C 0.03912(9) 0.3455(2) 0.08651(8) 0.0211(3) Uani 1 1 d . . .
C8 C -0.03952(9) 0.3775(2) 0.10634(8) 0.0234(3) Uani 1 1 d . . .
C9 C -0.11491(9) 0.2032(2) 0.08367(8) 0.0212(3) Uani 1 1 d . . .
C10 C -0.20071(8) 0.2366(2) 0.11049(7) 0.0187(3) Uani 1 1 d . . .
C11 C -0.27089(9) 0.0690(2) 0.08486(8) 0.0198(3) Uani 1 1 d . . .
C12 C -0.35084(8) 0.0809(2) 0.10893(7) 0.0186(3) Uani 1 1 d . . .
C13 C -0.36324(8) 0.2661(2) 0.15923(7) 0.0183(3) Uani 1 1 d . . .
C14 C -0.29385(9) 0.4301(2) 0.18543(8) 0.0196(3) Uani 1 1 d . . .
C15 C -0.21286(9) 0.4157(2) 0.16088(8) 0.0199(3) Uani 1 1 d . . .
C16 C -0.42114(10) -0.2350(3) 0.02519(9) 0.0274(3) Uani 1 1 d . . .
C17 C -0.46441(10) 0.4595(3) 0.22279(9) 0.0276(3) Uani 1 1 d . . .
O1 O -0.44576(6) 0.26619(17) 0.17735(5) 0.0230(2) Uani 1 1 d . . .
O2 O -0.42194(6) -0.07460(16) 0.08844(6) 0.0250(2) Uani 1 1 d . . .
O3 O -0.10703(7) 0.02802(18) 0.04513(6) 0.0314(3) Uani 1 1 d . . .
Cl1 Cl 0.37796(2) 0.94675(6) 0.16259(2) 0.02741(12) Uani 1 1 d . . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.3833(19) . ?
C1 C2 1.3840(19) . ?
C1 Cl1 1.7396(13) . ?
C2 C3 1.3834(19) . ?
C3 C4 1.3923(18) . ?
C4 C5 1.4008(19) . ?
C4 C7 1.4651(18) . ?
C5 C6 1.3818(19) . ?
C7 C8 1.3283(18) . ?
C8 C9 1.4790(18) . ?
C9 O3 1.2263(16) . ?
C9 C10 1.4949(17) . ?
C10 C15 1.3881(18) . ?
C10 C11 1.4043(18) . ?
C11 C12 1.3745(18) . ?
C12 O2 1.3601(15) . ?
C12 C13 1.4144(18) . ?
C13 O1 1.3577(15) . ?
C13 C14 1.3835(18) . ?
C14 C15 1.3946(18) . ?
C16 O2 1.4303(17) . ?
C17 O1 1.4270(17) . ?

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
C6 C1 C2 121.23(12) . . ?
C6 C1 Cl1 119.71(10) . . ?
C2 C1 Cl1 119.05(10) . . ?
C3 C2 C1 119.21(12) . . ?
C2 C3 C4 121.16(13) . . ?
C3 C4 C5 118.13(12) . . ?
C3 C4 C7 118.80(12) . . ?
C5 C4 C7 123.07(12) . . ?
C6 C5 C4 121.34(12) . . ?
C5 C6 C1 118.92(13) . . ?
C8 C7 C4 127.14(13) . . ?
C7 C8 C9 120.58(13) . . ?
O3 C9 C8 120.99(12) . . ?
O3 C9 C10 119.42(11) . . ?
C8 C9 C10 119.56(11) . . ?
C15 C10 C11 119.12(11) . . ?
C15 C10 C9 124.05(11) . . ?
C11 C10 C9 116.78(11) . . ?
C12 C11 C10 120.85(12) . . ?
O2 C12 C11 125.23(12) . . ?
O2 C12 C13 115.14(11) . . ?
C11 C12 C13 119.63(11) . . ?
O1 C13 C14 125.26(12) . . ?
O1 C13 C12 115.00(11) . . ?
C14 C13 C12 119.74(11) . . ?
C13 C14 C15 120.10(12) . . ?
C10 C15 C14 120.55(12) . . ?
C13 O1 C17 117.06(10) . . ?
C12 O2 C16 116.74(10) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        26.15
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.041
####################################################################### 
# 
# 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/. 
# 
# Audit and citation data items have may 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_datam
_database_code_depnum_ccdc_archive 'CCDC 1024003'
_audit_update_record             
;
2014-09-12 deposited with the CCDC.
2014-11-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H8 Br Cl2 O'
_chemical_formula_sum            'C15 H8 Br Cl2 O'
_chemical_formula_weight         355.00

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/n

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

_cell_length_a                   3.8793(7)
_cell_length_b                   15.208(3)
_cell_length_c                   23.308(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.189(7)
_cell_angle_gamma                90.00
_cell_volume                     1374.1(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    173
_cell_measurement_reflns_used    12341
_cell_measurement_theta_min      3.2
_cell_measurement_theta_max      30.7

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.716
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             700
_exptl_absorpt_coefficient_mu    3.367
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      173
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       
;
XtaLABmini: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  
;
Rigaku Mercury375R (2x2 bin mode)
;
_diffrn_detector_area_resol_mean 13.6612
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            15978
_diffrn_reflns_av_R_equivalents  0.0708
_diffrn_reflns_av_sigmaI/netI    0.0690
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         3.20
_diffrn_reflns_theta_max         30.49
_reflns_number_total             4188
_reflns_number_gt                2830
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       
;
CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009)
;
_computing_structure_solution    'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(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)+(0.0317P)²+1.1957P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4188
_refine_ls_number_parameters     204
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0905
_refine_ls_R_factor_gt           0.0509
_refine_ls_wR_factor_ref         0.1030
_refine_ls_wR_factor_gt          0.0892
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_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
H5 H 0.298(9) 0.415(2) -0.0987(16) 0.043(11) Uiso 1 1 d . . .
H6 H 0.576(8) 0.353(2) -0.0292(13) 0.022(8) Uiso 1 1 d . . .
H7 H 0.806(9) 0.288(2) 0.0491(15) 0.035(10) Uiso 1 1 d . . .
H8 H 0.440(9) 0.119(2) -0.1038(14) 0.030(9) Uiso 1 1 d . . .
H1 H -0.359(8) 0.687(2) -0.1213(14) 0.026(8) Uiso 1 1 d . . .
H2 H -0.407(8) 0.737(2) -0.2151(14) 0.032(9) Uiso 1 1 d . . .
H3 H -0.252(8) 0.636(2) -0.2902(14) 0.025(8) Uiso 1 1 d . . .
H4 H -0.054(10) 0.377(2) -0.2011(16) 0.047(11) Uiso 1 1 d . . .
C1 C -0.3288(9) 0.6774(2) -0.20770(16) 0.0366(8) Uani 1 1 d . . .
C2 C -0.2926(9) 0.6503(2) -0.15102(15) 0.0315(7) Uani 1 1 d . . .
C3 C -0.1761(8) 0.5661(2) -0.13881(12) 0.0253(7) Uani 1 1 d . . .
C4 C -0.0864(7) 0.5058(2) -0.18131(12) 0.0231(6) Uani 1 1 d . . .
C5 C -0.1240(8) 0.5379(2) -0.23790(13) 0.0278(7) Uani 1 1 d . . .
C6 C -0.2420(9) 0.6210(2) -0.25147(15) 0.0346(8) Uani 1 1 d . . .
C7 C 0.0233(8) 0.4148(2) -0.17149(13) 0.0274(7) Uani 1 1 d . . .
C8 C 0.2055(9) 0.3799(2) -0.12806(14) 0.0276(7) Uani 1 1 d . . .
C9 C 0.2917(8) 0.2850(2) -0.12791(13) 0.0257(7) Uani 1 1 d . . .
C10 C 0.4670(7) 0.2451(2) -0.07594(12) 0.0232(6) Uani 1 1 d . . .
C11 C 0.5822(8) 0.2939(2) -0.02824(13) 0.0267(7) Uani 1 1 d . . .
C12 C 0.7329(8) 0.2534(2) 0.01919(13) 0.0282(7) Uani 1 1 d . . .
C13 C 0.7670(8) 0.1635(2) 0.01958(13) 0.0267(7) Uani 1 1 d . . .
C14 C 0.6626(9) 0.1119(2) -0.02727(15) 0.0330(7) Uani 1 1 d . . .
C15 C 0.5115(9) 0.1542(2) -0.07444(14) 0.0305(7) Uani 1 1 d . . .
O1 O 0.2186(7) 0.23929(15) -0.16965(10) 0.0388(6) Uani 1 1 d . . .
Cl1 Cl -0.0098(2) 0.47113(6) -0.29469(3) 0.0371(2) Uani 1 1 d . . .
Cl2 Cl -0.1549(2) 0.53757(5) -0.06580(3) 0.0327(2) Uani 1 1 d . . .
Br1 Br 0.96180(9) 0.10799(2) 0.086229(15) 0.03700(12) Uani 1 1 d . . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.384(5) . ?
C1 C2 1.386(5) . ?
C1 H2 0.97(3) . ?
C2 C3 1.384(4) . ?
C2 H1 0.93(3) . ?
C3 C4 1.403(4) . ?
C3 Cl2 1.755(3) . ?
C4 C5 1.409(4) . ?
C4 C7 1.463(4) . ?
C5 C6 1.377(5) . ?
C5 Cl1 1.739(3) . ?
C6 H3 0.93(3) . ?
C7 C8 1.324(4) . ?
C7 H4 0.94(4) . ?
C8 C9 1.481(4) . ?
C8 H5 0.93(4) . ?
C9 O1 1.220(4) . ?
C9 C10 1.495(4) . ?
C10 C15 1.392(4) . ?
C10 C11 1.396(4) . ?
C11 C12 1.377(4) . ?
C11 H6 0.89(3) . ?
C12 C13 1.374(5) . ?
C12 H7 0.91(3) . ?
C13 C14 1.392(5) . ?
C13 Br1 1.899(3) . ?
C14 C15 1.385(5) . ?
C15 H8 0.91(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
C6 C1 C2 120.0(3) . . ?
C6 C1 H2 122(2) . . ?
C2 C1 H2 118(2) . . ?
C3 C2 C1 119.5(3) . . ?
C3 C2 H1 120(2) . . ?
C1 C2 H1 121(2) . . ?
C2 C3 C4 123.2(3) . . ?
C2 C3 Cl2 115.5(2) . . ?
C4 C3 Cl2 121.3(2) . . ?
C3 C4 C5 114.5(3) . . ?
C3 C4 C7 125.9(3) . . ?
C5 C4 C7 119.6(3) . . ?
C6 C5 C4 123.7(3) . . ?
C6 C5 Cl1 117.0(2) . . ?
C4 C5 Cl1 119.3(2) . . ?
C5 C6 C1 119.2(3) . . ?
C5 C6 H3 116(2) . . ?
C1 C6 H3 124(2) . . ?
C8 C7 C4 130.0(3) . . ?
C8 C7 H4 117(2) . . ?
C4 C7 H4 113(2) . . ?
C7 C8 C9 120.5(3) . . ?
C7 C8 H5 121(2) . . ?
C9 C8 H5 118(2) . . ?
O1 C9 C8 120.5(3) . . ?
O1 C9 C10 120.0(3) . . ?
C8 C9 C10 119.6(3) . . ?
C15 C10 C11 118.2(3) . . ?
C15 C10 C9 118.4(3) . . ?
C11 C10 C9 123.4(3) . . ?
C12 C11 C10 120.9(3) . . ?
C12 C11 H6 119(2) . . ?
C10 C11 H6 120(2) . . ?
C13 C12 C11 119.3(3) . . ?
C13 C12 H7 123(2) . . ?
C11 C12 H7 118(2) . . ?
C12 C13 C14 122.0(3) . . ?
C12 C13 Br1 118.9(2) . . ?
C14 C13 Br1 119.1(2) . . ?
C15 C14 C13 117.6(3) . . ?
C14 C15 C10 121.9(3) . . ?
C14 C15 H8 116(2) . . ?
C10 C15 H8 123(2) . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        30.49
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.802
_refine_diff_density_min         -0.608
_refine_diff_density_rms         0.100
####################################################################### 
# 
# 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/. 
# 
# Audit and citation data items have may 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_datam
_audit_block_doi                 10.5517/cc13ckdf
_database_code_depnum_ccdc_archive 'CCDC 1024004'
_audit_update_record             
;
2014-11-05 deposited with the CCDC.
2014-11-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H8 F N3 O2'
_chemical_formula_weight         269.23

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/c

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

_cell_length_a                   7.820(5)
_cell_length_b                   24.093(13)
_cell_length_c                   7.286(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 117.167(6)
_cell_angle_gamma                90.00
_cell_volume                     1221.3(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    150
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Plate
_exptl_crystal_colour            Red
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.464
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             552
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150
_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12788
_diffrn_reflns_av_R_equivalents  0.0638
_diffrn_reflns_av_sigmaI/netI    0.0382
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         1.69
_diffrn_reflns_theta_max         27.45
_reflns_number_total             2795
_reflns_number_gt                2446
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(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)+(0.0805P)²+0.1567P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2795
_refine_ls_number_parameters     185
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0551
_refine_ls_R_factor_gt           0.0467
_refine_ls_wR_factor_ref         0.1477
_refine_ls_wR_factor_gt          0.1343
_refine_ls_goodness_of_fit_ref   1.129
_refine_ls_restrained_S_all      1.129
_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
H5 H 0.881(3) 0.3555(7) 1.187(3) 0.033(5) Uiso 1 1 d . . .
O1 O 0.33545(16) 0.11423(4) 0.95644(18) 0.0322(3) Uani 1 1 d . . .
F F 0.69305(13) 0.11214(4) 1.03157(16) 0.0335(3) Uani 1 1 d . . .
C13 C 0.50505(19) 0.19508(6) 0.9747(2) 0.0207(3) Uani 1 1 d . . .
N3 N 0.33775(17) 0.16526(5) 0.96380(19) 0.0252(3) Uani 1 1 d . . .
C11 C 0.8323(2) 0.19768(6) 1.0298(2) 0.0236(3) Uani 1 1 d . . .
H8 H 0.9457 0.1794 1.0553 0.028 Uiso 1 1 calc R . .
C14 C 0.4922(2) 0.25237(6) 0.9524(2) 0.0211(3) Uani 1 1 d . . .
H7 H 0.3777 0.2704 0.9241 0.025 Uiso 1 1 calc R . .
N1 N 0.63129(17) 0.34124(5) 0.94532(19) 0.0239(3) Uani 1 1 d . . .
C8 C 0.7706(2) 0.37102(6) 1.0707(2) 0.0235(3) Uani 1 1 d . . .
C12 C 0.6750(2) 0.16787(6) 1.0116(2) 0.0222(3) Uani 1 1 d . . .
C7 C 0.6342(2) 0.46042(6) 0.8822(2) 0.0243(3) Uani 1 1 d . . .
H4 H 0.5365 0.4408 0.7762 0.029 Uiso 1 1 calc R . .
C5 C 0.9179(2) 0.46140(6) 1.2131(2) 0.0267(3) Uani 1 1 d . . .
H3 H 1.0097 0.4424 1.3265 0.032 Uiso 1 1 calc R . .
C10 C 0.8217(2) 0.25493(6) 1.0101(2) 0.0227(3) Uani 1 1 d . . .
H6 H 0.9279 0.2750 1.0218 0.027 Uiso 1 1 calc R . .
C3 C 0.6430(2) 0.51762(6) 0.8700(2) 0.0255(3) Uani 1 1 d . . .
H2 H 0.5522 0.5366 0.7559 0.031 Uiso 1 1 calc R . .
C9 C 0.6518(2) 0.28269(6) 0.9727(2) 0.0214(3) Uani 1 1 d . . .
O2 O 0.20542(16) 0.19305(5) 0.9616(2) 0.0400(3) Uani 1 1 d . . .
C4 C 0.9271(2) 0.51880(6) 1.2037(2) 0.0274(3) Uani 1 1 d . . .
H1 H 1.0234 0.5384 1.3111 0.033 Uiso 1 1 calc R . .
C1 C 0.8058(2) 0.60622(6) 1.0194(2) 0.0271(3) Uani 1 1 d . . .
C2 C 0.7908(2) 0.54664(6) 1.0322(2) 0.0243(3) Uani 1 1 d . . .
C6 C 0.7720(2) 0.43195(6) 1.0537(2) 0.0225(3) Uani 1 1 d . . .
N2 N 0.8231(2) 0.65334(6) 1.0116(2) 0.0343(3) Uani 1 1 d . . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N3 1.2304(17) . ?
F C12 1.3509(17) . ?
C13 C14 1.388(2) . ?
C13 C12 1.393(2) . ?
C13 N3 1.4626(19) . ?
N3 O2 1.2265(18) . ?
C11 C12 1.378(2) . ?
C11 C10 1.385(2) . ?
C14 C9 1.395(2) . ?
N1 C8 1.276(2) . ?
N1 C9 1.4234(19) . ?
C8 C6 1.474(2) . ?
C7 C3 1.385(2) . ?
C7 C6 1.401(2) . ?
C5 C4 1.388(2) . ?
C5 C6 1.394(2) . ?
C10 C9 1.399(2) . ?
C3 C2 1.405(2) . ?
C4 C2 1.390(2) . ?
C1 N2 1.148(2) . ?
C1 C2 1.447(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C14 C13 C12 120.16(12) . . ?
C14 C13 N3 117.83(12) . . ?
C12 C13 N3 121.99(14) . . ?
O2 N3 O1 123.33(12) . . ?
O2 N3 C13 117.45(13) . . ?
O1 N3 C13 119.22(12) . . ?
C12 C11 C10 120.04(13) . . ?
C13 C14 C9 119.65(13) . . ?
C8 N1 C9 116.89(12) . . ?
N1 C8 C6 122.45(13) . . ?
F C12 C11 117.58(12) . . ?
F C12 C13 122.15(12) . . ?
C11 C12 C13 120.28(14) . . ?
C3 C7 C6 120.27(13) . . ?
C4 C5 C6 120.46(13) . . ?
C11 C10 C9 120.19(13) . . ?
C7 C3 C2 119.16(13) . . ?
C14 C9 C10 119.66(14) . . ?
C14 C9 N1 117.78(12) . . ?
C10 C9 N1 122.51(12) . . ?
C5 C4 C2 119.31(13) . . ?
N2 C1 C2 178.14(15) . . ?
C4 C2 C3 120.97(14) . . ?
C4 C2 C1 119.03(13) . . ?
C3 C2 C1 119.97(13) . . ?
C5 C6 C7 119.82(14) . . ?
C5 C6 C8 118.12(13) . . ?
C7 C6 C8 122.05(13) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C14 C13 N3 O2 -8.92(18) . . . . ?
C12 C13 N3 O2 169.37(14) . . . . ?
C14 C13 N3 O1 170.77(12) . . . . ?
C12 C13 N3 O1 -10.94(19) . . . . ?
C12 C13 C14 C9 -1.71(19) . . . . ?
N3 C13 C14 C9 176.61(12) . . . . ?
C9 N1 C8 C6 177.06(12) . . . . ?
C10 C11 C12 F 179.82(12) . . . . ?
C10 C11 C12 C13 -0.4(2) . . . . ?
C14 C13 C12 F -179.12(12) . . . . ?
N3 C13 C12 F 2.6(2) . . . . ?
C14 C13 C12 C11 1.1(2) . . . . ?
N3 C13 C12 C11 -177.14(12) . . . . ?
C12 C11 C10 C9 0.3(2) . . . . ?
C6 C7 C3 C2 -0.4(2) . . . . ?
C13 C14 C9 C10 1.6(2) . . . . ?
C13 C14 C9 N1 178.98(11) . . . . ?
C11 C10 C9 C14 -0.9(2) . . . . ?
C11 C10 C9 N1 -178.15(12) . . . . ?
C8 N1 C9 C14 138.39(14) . . . . ?
C8 N1 C9 C10 -44.31(19) . . . . ?
C6 C5 C4 C2 -0.9(2) . . . . ?
C5 C4 C2 C3 0.8(2) . . . . ?
C5 C4 C2 C1 -177.46(13) . . . . ?
C7 C3 C2 C4 -0.1(2) . . . . ?
C7 C3 C2 C1 178.12(13) . . . . ?
N2 C1 C2 C4 38(5) . . . . ?
N2 C1 C2 C3 -140(5) . . . . ?
C4 C5 C6 C7 0.4(2) . . . . ?
C4 C5 C6 C8 179.29(13) . . . . ?
C3 C7 C6 C5 0.3(2) . . . . ?
C3 C7 C6 C8 -178.56(13) . . . . ?
N1 C8 C6 C5 171.61(14) . . . . ?
N1 C8 C6 C7 -9.5(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.45
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.072
####################################################################### 
# 
# 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/. 
# 
# Audit and citation data items have may 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_12
_database_code_depnum_ccdc_archive 'CCDC 1027956'
_audit_update_record             
;
2014-10-07 deposited with the CCDC.
2014-11-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H18 N2 O6'
_chemical_formula_weight         358.34

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                   8.781(8)
_cell_length_b                   9.080(10)
_cell_length_c                   11.641(12)
_cell_angle_alpha                86.17(5)
_cell_angle_beta                 69.02(4)
_cell_angle_gamma                73.38(4)
_cell_volume                     829.8(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2232
_cell_measurement_theta_min      2.9
_cell_measurement_theta_max      33.5

_exptl_crystal_description       Block
_exptl_crystal_colour            Red
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             376
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_type   multi-scan
# Example: '(North et al., 1968)'
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_absorpt_correction_T_min  0.9764
_exptl_absorpt_correction_T_max  0.9785

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       
;
XtaLABmini: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  
;
Rigaku Mercury375R (2x2 bin mode)
;
_diffrn_detector_area_resol_mean 13.6612
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7795
_diffrn_reflns_av_R_equivalents  0.0519
_diffrn_reflns_av_sigmaI/netI    0.0486
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.88
_diffrn_reflns_theta_max         26.00
_reflns_number_total             3257
_reflns_number_gt                2421
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       
;
CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009)
;
_computing_structure_solution    'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(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)+(0.1124P)²+0.0945P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3257
_refine_ls_number_parameters     237
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0825
_refine_ls_R_factor_gt           0.0608
_refine_ls_wR_factor_ref         0.2010
_refine_ls_wR_factor_gt          0.1693
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_restrained_S_all      1.085
_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
C19 C 0.8293(3) 0.0983(2) 0.14329(19) 0.0311(5) Uani 1 1 d . . .
H17 H 0.8533 0.0551 0.0645 0.037 Uiso 1 1 calc R . .
C20 C 0.8504(3) 0.2911(2) 0.26614(19) 0.0300(5) Uani 1 1 d . . .
C21 C 0.9964(3) 0.4836(3) 0.1668(2) 0.0412(6) Uani 1 1 d . . .
H18 H 0.9206 0.5271 0.1210 0.062 Uiso 1 1 calc R . .
H19 H 1.0967 0.4061 0.1145 0.062 Uiso 1 1 calc R . .
H20 H 1.0319 0.5656 0.1915 0.062 Uiso 1 1 calc R . .
C22 C 0.3290(3) 0.2198(2) 0.26656(19) 0.0304(5) Uani 1 1 d . . .
C23 C 0.2922(3) 0.0329(3) 0.1478(2) 0.0359(5) Uani 1 1 d . . .
H21 H 0.3055 -0.0083 0.0708 0.043 Uiso 1 1 calc R . .
C24 C 0.4622(3) 0.4311(3) 0.1842(2) 0.0359(5) Uani 1 1 d . . .
H22 H 0.4800 0.4015 0.1026 0.043 Uiso 1 1 calc R . .
C25 C 0.6842(3) -0.1006(2) 0.23730(18) 0.0294(5) Uani 1 1 d . . .
C26 C 0.7020(3) 0.1015(2) 0.36223(19) 0.0327(5) Uani 1 1 d . . .
H23 H 0.6387 0.0605 0.4348 0.039 Uiso 1 1 calc R . .
C27 C 0.3501(3) 0.1585(2) 0.15334(19) 0.0341(5) Uani 1 1 d . . .
H24 H 0.4046 0.2030 0.0794 0.041 Uiso 1 1 calc R . .
C28 C 0.3878(3) 0.3533(2) 0.2756(2) 0.0328(5) Uani 1 1 d . . .
H25 H 0.3700 0.3868 0.3562 0.039 Uiso 1 1 calc R . .
C29 C 0.8837(3) 0.2236(2) 0.15088(19) 0.0329(5) Uani 1 1 d . . .
H26 H 0.9446 0.2652 0.0776 0.039 Uiso 1 1 calc R . .
C30 C 0.1937(3) 0.0265(3) 0.3692(2) 0.0373(5) Uani 1 1 d . . .
H27 H 0.1405 -0.0195 0.4427 0.045 Uiso 1 1 calc R . .
C31 C 0.2152(3) -0.0304(2) 0.2558(2) 0.0313(5) Uani 1 1 d . . .
C32 C 0.8652(4) 0.4849(3) 0.3942(2) 0.0485(6) Uani 1 1 d . . .
H28 H 0.9010 0.4075 0.4492 0.073 Uiso 1 1 calc R . .
H29 H 0.7421 0.5316 0.4298 0.073 Uiso 1 1 calc R . .
H30 H 0.9238 0.5647 0.3841 0.073 Uiso 1 1 calc R . .
C33 C 0.7396(3) 0.0329(2) 0.24829(18) 0.0286(5) Uani 1 1 d . . .
C34 C 0.2513(3) 0.1520(3) 0.37351(19) 0.0360(5) Uani 1 1 d . . .
H31 H 0.2374 0.1924 0.4510 0.043 Uiso 1 1 calc R . .
C35 C 0.7546(3) 0.2277(2) 0.37213(19) 0.0332(5) Uani 1 1 d . . .
H32 H 0.7262 0.2728 0.4511 0.040 Uiso 1 1 calc R . .
C36 C 0.5189(3) 0.5615(2) 0.2026(2) 0.0343(5) Uani 1 1 d . . .
N1 N 0.1516(2) -0.1611(2) 0.25044(19) 0.0392(5) Uani 1 1 d . . .
N3 N 0.9077(3) 0.4125(2) 0.27550(17) 0.0380(5) Uani 1 1 d . . .
O1 O 0.6077(2) -0.16100(18) 0.33592(14) 0.0421(4) Uani 1 1 d . . .
H8 H 0.5839 -0.2360 0.3194 0.063 Uiso 1 1 d R . .
O2 O 0.7128(2) -0.15364(18) 0.13120(14) 0.0418(4) Uani 1 1 d . . .
O3 O 0.4879(2) 0.61112(18) 0.30916(13) 0.0408(4) Uani 1 1 d . . .
O4 O 0.6019(2) 0.61903(19) 0.10474(14) 0.0471(5) Uani 1 1 d . . .
H9 H 0.6317 0.6889 0.1224 0.071 Uiso 1 1 d R . .
O5 O 0.0709(2) -0.2097(2) 0.34791(17) 0.0547(5) Uani 1 1 d . . .
O6 O 0.1821(3) -0.2177(2) 0.14955(17) 0.0583(6) Uani 1 1 d . . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C19 C29 1.373(3) . ?
C19 C33 1.396(3) . ?
C19 H17 0.9500 . ?
C20 N3 1.361(3) . ?
C20 C29 1.410(3) . ?
C20 C35 1.414(3) . ?
C21 N3 1.448(3) . ?
C21 H18 0.9800 . ?
C21 H19 0.9800 . ?
C21 H20 0.9800 . ?
C22 C34 1.387(3) . ?
C22 C27 1.395(3) . ?
C22 C28 1.470(3) . ?
C23 C31 1.374(3) . ?
C23 C27 1.388(3) . ?
C23 H21 0.9500 . ?
C24 C28 1.313(3) . ?
C24 C36 1.464(3) . ?
C24 H22 0.9500 . ?
C25 O2 1.268(3) . ?
C25 O1 1.282(3) . ?
C25 C33 1.457(3) . ?
C26 C35 1.378(3) . ?
C26 C33 1.392(3) . ?
C26 H23 0.9500 . ?
C27 H24 0.9500 . ?
C28 H25 0.9500 . ?
C29 H26 0.9500 . ?
C30 C31 1.379(3) . ?
C30 C34 1.383(3) . ?
C30 H27 0.9500 . ?
C31 N1 1.461(3) . ?
C32 N3 1.447(3) . ?
C32 H28 0.9800 . ?
C32 H29 0.9800 . ?
C32 H30 0.9800 . ?
C34 H31 0.9500 . ?
C35 H32 0.9500 . ?
C36 O3 1.256(3) . ?
C36 O4 1.283(3) . ?
N1 O6 1.222(3) . ?
N1 O5 1.233(3) . ?
O1 H8 0.8197 . ?
O4 H9 0.8155 . ?

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
C29 C19 C33 121.8(2) . . ?
C29 C19 H17 119.1 . . ?
C33 C19 H17 119.1 . . ?
N3 C20 C29 121.56(19) . . ?
N3 C20 C35 121.1(2) . . ?
C29 C20 C35 117.3(2) . . ?
N3 C21 H18 109.5 . . ?
N3 C21 H19 109.5 . . ?
H18 C21 H19 109.5 . . ?
N3 C21 H20 109.5 . . ?
H18 C21 H20 109.5 . . ?
H19 C21 H20 109.5 . . ?
C34 C22 C27 118.9(2) . . ?
C34 C22 C28 119.2(2) . . ?
C27 C22 C28 121.9(2) . . ?
C31 C23 C27 118.7(2) . . ?
C31 C23 H21 120.6 . . ?
C27 C23 H21 120.6 . . ?
C28 C24 C36 122.8(2) . . ?
C28 C24 H22 118.6 . . ?
C36 C24 H22 118.6 . . ?
O2 C25 O1 121.95(19) . . ?
O2 C25 C33 119.40(19) . . ?
O1 C25 C33 118.65(19) . . ?
C35 C26 C33 121.5(2) . . ?
C35 C26 H23 119.3 . . ?
C33 C26 H23 119.3 . . ?
C23 C27 C22 120.6(2) . . ?
C23 C27 H24 119.7 . . ?
C22 C27 H24 119.7 . . ?
C24 C28 C22 126.9(2) . . ?
C24 C28 H25 116.6 . . ?
C22 C28 H25 116.6 . . ?
C19 C29 C20 120.8(2) . . ?
C19 C29 H26 119.6 . . ?
C20 C29 H26 119.6 . . ?
C31 C30 C34 118.5(2) . . ?
C31 C30 H27 120.7 . . ?
C34 C30 H27 120.7 . . ?
C23 C31 C30 122.2(2) . . ?
C23 C31 N1 118.8(2) . . ?
C30 C31 N1 118.9(2) . . ?
N3 C32 H28 109.5 . . ?
N3 C32 H29 109.5 . . ?
H28 C32 H29 109.5 . . ?
N3 C32 H30 109.5 . . ?
H28 C32 H30 109.5 . . ?
H29 C32 H30 109.5 . . ?
C26 C33 C19 117.8(2) . . ?
C26 C33 C25 121.71(19) . . ?
C19 C33 C25 120.49(19) . . ?
C30 C34 C22 121.1(2) . . ?
C30 C34 H31 119.5 . . ?
C22 C34 H31 119.5 . . ?
C26 C35 C20 120.8(2) . . ?
C26 C35 H32 119.6 . . ?
C20 C35 H32 119.6 . . ?
O3 C36 O4 123.1(2) . . ?
O3 C36 C24 120.7(2) . . ?
O4 C36 C24 116.1(2) . . ?
O6 N1 O5 123.1(2) . . ?
O6 N1 C31 118.40(19) . . ?
O5 N1 C31 118.5(2) . . ?
C20 N3 C32 120.72(19) . . ?
C20 N3 C21 121.1(2) . . ?
C32 N3 C21 117.8(2) . . ?
C25 O1 H8 110.7 . . ?
C36 O4 H9 110.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C31 C23 C27 C22 -0.6(3) . . . . ?
C34 C22 C27 C23 0.9(3) . . . . ?
C28 C22 C27 C23 -179.55(19) . . . . ?
C36 C24 C28 C22 -178.95(19) . . . . ?
C34 C22 C28 C24 -179.5(2) . . . . ?
C27 C22 C28 C24 0.9(4) . . . . ?
C33 C19 C29 C20 -0.1(3) . . . . ?
N3 C20 C29 C19 178.0(2) . . . . ?
C35 C20 C29 C19 -2.0(3) . . . . ?
C27 C23 C31 C30 0.0(3) . . . . ?
C27 C23 C31 N1 179.05(18) . . . . ?
C34 C30 C31 C23 0.3(3) . . . . ?
C34 C30 C31 N1 -178.76(19) . . . . ?
C35 C26 C33 C19 -1.5(3) . . . . ?
C35 C26 C33 C25 -179.97(19) . . . . ?
C29 C19 C33 C26 1.8(3) . . . . ?
C29 C19 C33 C25 -179.68(19) . . . . ?
O2 C25 C33 C26 175.88(19) . . . . ?
O1 C25 C33 C26 -4.2(3) . . . . ?
O2 C25 C33 C19 -2.5(3) . . . . ?
O1 C25 C33 C19 177.39(18) . . . . ?
C31 C30 C34 C22 0.0(3) . . . . ?
C27 C22 C34 C30 -0.6(3) . . . . ?
C28 C22 C34 C30 179.83(19) . . . . ?
C33 C26 C35 C20 -0.6(3) . . . . ?
N3 C20 C35 C26 -177.7(2) . . . . ?
C29 C20 C35 C26 2.3(3) . . . . ?
C28 C24 C36 O3 -4.8(4) . . . . ?
C28 C24 C36 O4 174.6(2) . . . . ?
C23 C31 N1 O6 6.2(3) . . . . ?
C30 C31 N1 O6 -174.8(2) . . . . ?
C23 C31 N1 O5 -174.4(2) . . . . ?
C30 C31 N1 O5 4.7(3) . . . . ?
C29 C20 N3 C32 177.0(2) . . . . ?
C35 C20 N3 C32 -3.0(3) . . . . ?
C29 C20 N3 C21 3.9(3) . . . . ?
C35 C20 N3 C21 -176.02(19) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.342
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.074
####################################################################### 
# 
# 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/. 
# 
# Audit and citation data items have may 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_33
_database_code_depnum_ccdc_archive 'CCDC 1033507'
_audit_update_record             
;
2014-11-10 deposited with the CCDC.
2014-11-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H16 F4 N2 O4'
_chemical_formula_weight         472.39

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
F F 0.0171 0.0103 '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                   6.916(4)
_cell_length_b                   6.922(4)
_cell_length_c                   11.215(8)
_cell_angle_alpha                88.869(17)
_cell_angle_beta                 88.15(2)
_cell_angle_gamma                72.09(2)
_cell_volume                     510.5(6)
_cell_formula_units_Z            1
_cell_measurement_temperature    150
_cell_measurement_reflns_used    1826
_cell_measurement_theta_min      3.1
_cell_measurement_theta_max      33.7

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.537
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             242
_exptl_absorpt_coefficient_mu    0.130
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.841
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       
;
XtaLABmini: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  
;
Rigaku Mercury375R (2x2 bin mode)
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean 13.6612
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4790
_diffrn_reflns_av_R_equivalents  0.0974
_diffrn_reflns_av_sigmaI/netI    0.0758
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.82
_diffrn_reflns_theta_max         26.00
_reflns_number_total             2004
_reflns_number_gt                1830
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       
;
CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009)
;
_computing_structure_solution    'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?


_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(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)+(0.0694P)²+0.0903P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2004
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0543
_refine_ls_R_factor_gt           0.0513
_refine_ls_wR_factor_ref         0.1501
_refine_ls_wR_factor_gt          0.1458
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_restrained_S_all      1.088
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.001

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
C001 C 0.1828(2) 0.5415(2) 0.31940(12) 0.0243(3) Uani 1 1 d . . .
F1 F -0.15103(15) 0.56082(15) 0.26014(9) 0.0453(3) Uani 1 1 d . . .
F2 F -0.14752(16) 0.23297(15) 0.38481(10) 0.0476(3) Uani 1 1 d . . .
C004 C 0.0172(2) 0.4688(2) 0.32071(12) 0.0278(3) Uani 1 1 d . . .
C005 C 0.3488(2) 0.4369(2) 0.38806(13) 0.0284(3) Uani 1 1 d . . .
H005 H 0.4629 0.4812 0.3878 0.034 Uiso 1 1 calc R . .
C006 C 0.1802(3) 0.1967(2) 0.45587(14) 0.0328(4) Uani 1 1 d . . .
H006 H 0.1784 0.0828 0.5008 0.039 Uiso 1 1 calc R . .
C007 C 0.4792(2) 1.41038(18) 0.02981(11) 0.0241(3) Uani 1 1 d . . .
O1 O 0.3518(2) 0.77539(18) 0.26625(11) 0.0449(4) Uani 1 1 d . . .
H1 H 0.3505 0.8754 0.2255 0.067 Uiso 1 1 calc R . .
N1 N 0.4024(2) 1.07639(17) 0.14314(11) 0.0314(3) Uani 1 1 d . . .
C010 C 0.6207(3) 1.2796(2) 0.10354(15) 0.0353(4) Uani 1 1 d . . .
H010 H 0.7445 1.3015 0.1161 0.042 Uiso 1 1 calc R . .
C011 C 0.0177(2) 0.2977(2) 0.38725(13) 0.0306(3) Uani 1 1 d . . .
C012 C 0.3002(2) 1.3651(2) 0.01357(14) 0.0313(4) Uani 1 1 d . . .
H012 H 0.2020 1.4464 -0.0360 0.038 Uiso 1 1 calc R . .
C013 C 0.1897(2) 0.7247(2) 0.24697(13) 0.0294(4) Uani 1 1 d . . .
O2 O 0.0599(2) 0.8115(2) 0.17730(13) 0.0556(4) Uani 1 1 d . . .
C015 C 0.3462(2) 0.2680(2) 0.45661(14) 0.0339(4) Uani 1 1 d . . .
H015 H 0.4567 0.2027 0.5032 0.041 Uiso 1 1 calc R . .
C016 C 0.2675(2) 1.1982(2) 0.07139(14) 0.0329(4) Uani 1 1 d . . .
H016 H 0.1462 1.1705 0.0594 0.039 Uiso 1 1 calc R . .
C017 C 0.5758(3) 1.1162(2) 0.15828(15) 0.0384(4) Uani 1 1 d . . .
H017 H 0.6715 1.0309 0.2077 0.046 Uiso 1 1 calc R . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C001 C004 1.384(2) . ?
C001 C005 1.400(2) . ?
C001 C013 1.505(2) . ?
F1 C004 1.3414(18) . ?
F2 C011 1.3507(19) . ?
C004 C011 1.387(2) . ?
C005 C015 1.391(2) . ?
C006 C011 1.377(2) . ?
C006 C015 1.382(2) . ?
C007 C012 1.385(2) . ?
C007 C010 1.392(2) . ?
C007 C007 1.498(3) 2_685 ?
O1 C013 1.299(2) . ?
N1 C017 1.327(2) . ?
N1 C016 1.329(2) . ?
C010 C017 1.389(2) . ?
C012 C016 1.388(2) . ?
C013 O2 1.214(2) . ?

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
C004 C001 C005 117.60(13) . . ?
C004 C001 C013 122.50(13) . . ?
C005 C001 C013 119.89(14) . . ?
F1 C004 C001 122.20(13) . . ?
F1 C004 C011 116.95(14) . . ?
C001 C004 C011 120.84(13) . . ?
C015 C005 C001 121.18(14) . . ?
C011 C006 C015 118.61(14) . . ?
C012 C007 C010 116.75(13) . . ?
C012 C007 C007 121.95(16) . 2_685 ?
C010 C007 C007 121.29(16) . 2_685 ?
C017 N1 C016 118.03(13) . . ?
C017 C010 C007 119.62(15) . . ?
F2 C011 C006 120.25(14) . . ?
F2 C011 C004 118.34(14) . . ?
C006 C011 C004 121.40(15) . . ?
C007 C012 C016 119.99(14) . . ?
O2 C013 O1 124.45(14) . . ?
O2 C013 C001 123.42(15) . . ?
O1 C013 C001 112.11(13) . . ?
C006 C015 C005 120.33(14) . . ?
N1 C016 C012 122.68(15) . . ?
N1 C017 C010 122.92(15) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.373
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.069
####################################################################### 
# 
# 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/. 
# 
# Audit and citation data items have may 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_46
_database_code_depnum_ccdc_archive 'CCDC 1033508'
_audit_update_record             
;
2014-11-10 deposited with the CCDC.
2014-11-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H24 N2 O2'
_chemical_formula_weight         444.51

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c

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

_cell_length_a                   14.118(12)
_cell_length_b                   5.881(5)
_cell_length_c                   15.040(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 113.629(10)
_cell_angle_gamma                90.00
_cell_volume                     1144.0(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    150
_cell_measurement_reflns_used    2981
_cell_measurement_theta_min      2.9
_cell_measurement_theta_max      33.5

_exptl_crystal_description       plate
_exptl_crystal_colour            brown
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             468
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.734
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       
;
XtaLABmini: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  
;
Rigaku Mercury375R (2x2 bin mode)
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean 13.6612
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10185
_diffrn_reflns_av_R_equivalents  0.0908
_diffrn_reflns_av_sigmaI/netI    0.0506
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.57
_diffrn_reflns_theta_max         25.99
_reflns_number_total             2241
_reflns_number_gt                1913
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       
;
CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009)
;
_computing_structure_solution    'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(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)+(0.1286P)²+2.6816P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2241
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0998
_refine_ls_R_factor_gt           0.0872
_refine_ls_wR_factor_ref         0.2901
_refine_ls_wR_factor_gt          0.2784
_refine_ls_goodness_of_fit_ref   1.149
_refine_ls_restrained_S_all      1.149
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C001 C 0.3579(3) 0.2061(6) 0.1739(3) 0.0277(9) Uani 1 1 d . . .
C002 C 0.3226(3) -0.0091(6) 0.1925(3) 0.0260(8) Uani 1 1 d . . .
C003 C 0.2648(3) -0.1518(7) 0.1136(3) 0.0276(8) Uani 1 1 d . . .
H003 H 0.2416 -0.2920 0.1254 0.033 Uiso 1 1 calc R . .
C004 C 0.4161(3) 0.3484(7) 0.2538(3) 0.0339(9) Uani 1 1 d . . .
H004 H 0.4394 0.4885 0.2421 0.041 Uiso 1 1 calc R . .
C005 C 0.2425(3) -0.0855(7) 0.0195(3) 0.0303(9) Uani 1 1 d . . .
O1 O 0.1864(3) -0.2284(5) -0.0538(2) 0.0448(9) Uani 1 1 d . . .
H1 H 0.1781 -0.1706 -0.1060 0.067 Uiso 1 1 calc R . .
C007 C 0.2775(3) 0.1283(7) 0.0014(3) 0.0326(9) Uani 1 1 d . . .
H007 H 0.2624 0.1734 -0.0621 0.039 Uiso 1 1 calc R . .
C008 C 0.3466(3) -0.0722(7) 0.2908(3) 0.0310(9) Uani 1 1 d . . .
H008 H 0.3240 -0.2114 0.3043 0.037 Uiso 1 1 calc R . .
C009 C 0.3336(3) 0.2697(7) 0.0770(3) 0.0305(9) Uani 1 1 d . . .
H009 H 0.3559 0.4097 0.0639 0.037 Uiso 1 1 calc R . .
C010 C 0.4382(3) 0.2832(8) 0.3472(3) 0.0391(10) Uani 1 1 d . . .
H010 H 0.4765 0.3780 0.3985 0.047 Uiso 1 1 calc R . .
C011 C 0.4025(3) 0.0704(8) 0.3653(3) 0.0364(10) Uani 1 1 d . . .
H011 H 0.4173 0.0268 0.4290 0.044 Uiso 1 1 calc R . .
N1 N 0.1250(2) 0.5800(6) 0.2567(2) 0.0313(8) Uani 1 1 d . . .
C014 C 0.0257(3) 0.5167(6) 0.0536(3) 0.0259(8) Uani 1 1 d . . .
C015 C 0.0939(3) 0.3551(7) 0.1138(3) 0.0301(9) Uani 1 1 d . . .
H015 H 0.1083 0.2232 0.0875 0.036 Uiso 1 1 calc R . .
C016 C 0.0600(3) 0.7350(7) 0.1989(3) 0.0345(9) Uani 1 1 d . . .
H016 H 0.0481 0.8664 0.2273 0.041 Uiso 1 1 calc R . .
C017 C 0.1400(3) 0.3926(7) 0.2133(3) 0.0317(9) Uani 1 1 d . . .
H017 H 0.1840 0.2810 0.2521 0.038 Uiso 1 1 calc R . .
C018 C 0.0089(3) 0.7111(7) 0.0985(3) 0.0331(9) Uani 1 1 d . . .
H018 H -0.0359 0.8239 0.0618 0.040 Uiso 1 1 calc R . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C001 C009 1.408(5) . ?
C001 C004 1.424(5) . ?
C001 C002 1.428(5) . ?
C002 C003 1.415(5) . ?
C002 C008 1.427(5) . ?
C003 C005 1.377(5) . ?
C004 C010 1.366(6) . ?
C005 O1 1.360(5) . ?
C005 C007 1.417(6) . ?
C007 C009 1.374(6) . ?
C008 C011 1.369(6) . ?
C010 C011 1.417(7) . ?
N1 C016 1.338(5) . ?
N1 C017 1.340(5) . ?
C014 C018 1.396(5) . ?
C014 C015 1.397(5) . ?
C014 C014 1.491(7) 3_565 ?
C015 C017 1.390(5) . ?
C016 C018 1.395(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
C009 C001 C004 122.4(4) . . ?
C009 C001 C002 118.7(3) . . ?
C004 C001 C002 118.9(4) . . ?
C003 C002 C008 122.2(4) . . ?
C003 C002 C001 119.3(3) . . ?
C008 C002 C001 118.5(3) . . ?
C005 C003 C002 120.8(4) . . ?
C010 C004 C001 121.3(4) . . ?
O1 C005 C003 118.5(4) . . ?
O1 C005 C007 121.8(3) . . ?
C003 C005 C007 119.7(4) . . ?
C009 C007 C005 120.5(4) . . ?
C011 C008 C002 120.6(4) . . ?
C007 C009 C001 121.0(4) . . ?
C004 C010 C011 119.6(4) . . ?
C008 C011 C010 121.1(4) . . ?
C016 N1 C017 116.4(3) . . ?
C018 C014 C015 116.7(3) . . ?
C018 C014 C014 121.9(4) . 3_565 ?
C015 C014 C014 121.4(4) . 3_565 ?
C017 C015 C014 119.6(4) . . ?
N1 C016 C018 123.9(4) . . ?
N1 C017 C015 123.8(4) . . ?
C016 C018 C014 119.5(4) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.99
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.377
_refine_diff_density_min         -0.439
_refine_diff_density_rms         0.124
