# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2016

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

data_3rcf172_0m
_database_code_depnum_ccdc_archive 'CCDC 1006037'
_audit_update_record             
;
2014-05-30 deposited with the CCDC.
2016-11-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H14 N2 O3'
_chemical_formula_sum            'C12 H14 N2 O3'
_chemical_formula_weight         234.25

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   P2(1)/c
_symmetry_space_group_name_Hall  '-P 2ybc '
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.0398(3)
_cell_length_b                   7.2748(3)
_cell_length_c                   17.0449(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.643(2)
_cell_angle_gamma                90.00
_cell_volume                     1108.19(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9984
_cell_measurement_theta_min      2.42
_cell_measurement_theta_max      27.54

_exptl_crystal_description       NEEDLE
_exptl_crystal_colour            YELLOW
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             496
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9554
_exptl_absorpt_correction_T_max  0.9818
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14308
_diffrn_reflns_av_R_equivalents  0.0210
_diffrn_reflns_av_sigmaI/netI    0.0132
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.28
_diffrn_reflns_theta_max         27.54
_reflns_number_total             2547
_reflns_number_gt                2386
_reflns_threshold_expression     >2sigma(I)

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

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0593P)²+0.3818P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    CONSTR
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2547
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0395
_refine_ls_R_factor_gt           0.0375
_refine_ls_wR_factor_ref         0.1014
_refine_ls_wR_factor_gt          0.0992
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.65219(8) 0.44571(11) 0.09679(4) 0.02296(18) Uani 1 1 d . . .
O2 O 0.95185(11) 0.25979(11) 0.07699(5) 0.0332(2) Uani 1 1 d . . .
O3 O 1.05127(9) 0.27789(12) 0.20034(5) 0.0326(2) Uani 1 1 d . . .
N1 N 0.70082(10) 0.57143(12) 0.03968(5) 0.0218(2) Uani 1 1 d . . .
N2 N 0.97325(10) 0.33883(12) 0.14103(5) 0.0213(2) Uani 1 1 d . . .
C1 C 0.72546(12) 0.88731(15) 0.01958(6) 0.0246(2) Uani 1 1 d . . .
H1A H 0.6930 1.0104 0.0307 0.030 Uiso 1 1 calc R . .
H1B H 0.7429 0.8808 -0.0351 0.030 Uiso 1 1 calc R . .
C2 C 0.61293(12) 0.74379(16) 0.03706(7) 0.0260(2) Uani 1 1 d . . .
H2A H 0.5790 0.7674 0.0875 0.031 Uiso 1 1 calc R . .
H2B H 0.5271 0.7398 -0.0046 0.031 Uiso 1 1 calc R . .
C3 C 0.73980(10) 0.48324(14) 0.17184(6) 0.0177(2) Uani 1 1 d . . .
H3 H 0.7032 0.5973 0.1927 0.021 Uiso 1 1 calc R . .
C4 C 0.72009(10) 0.32974(14) 0.22872(6) 0.0182(2) Uani 1 1 d . . .
C5 C 0.65505(12) 0.16319(15) 0.20205(6) 0.0227(2) Uani 1 1 d . . .
H5 H 0.6275 0.1430 0.1480 0.027 Uiso 1 1 calc R . .
C6 C 0.63109(13) 0.02695(15) 0.25594(7) 0.0261(2) Uani 1 1 d . . .
H6 H 0.5871 -0.0837 0.2377 0.031 Uiso 1 1 calc R . .
C7 C 0.67255(12) 0.05527(16) 0.33677(7) 0.0252(2) Uani 1 1 d . . .
H7 H 0.6560 -0.0358 0.3727 0.030 Uiso 1 1 calc R . .
C8 C 0.86492(12) 0.83122(14) 0.07706(6) 0.0222(2) Uani 1 1 d . . .
H8A H 0.8590 0.8725 0.1306 0.027 Uiso 1 1 calc R . .
H8B H 0.9551 0.8800 0.0604 0.027 Uiso 1 1 calc R . .
C9 C 0.86029(11) 0.62076(14) 0.07143(6) 0.0189(2) Uani 1 1 d . . .
H9 H 0.9266 0.5785 0.0346 0.023 Uiso 1 1 calc R . .
C10 C 0.89696(10) 0.51957(13) 0.15009(6) 0.0170(2) Uani 1 1 d . . .
H10 H 0.9565 0.5968 0.1901 0.020 Uiso 1 1 calc R . .
C11 C 0.76213(11) 0.35732(15) 0.30995(6) 0.0222(2) Uani 1 1 d . . .
H11 H 0.8059 0.4679 0.3283 0.027 Uiso 1 1 calc R . .
C12 C 0.73883(12) 0.21999(16) 0.36364(6) 0.0251(2) Uani 1 1 d . . .
H12 H 0.7678 0.2388 0.4177 0.030 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C3 1.4262(11) . ?
O1 N1 1.4512(11) . ?
O2 N2 1.2231(12) . ?
O3 N2 1.2255(12) . ?
N1 C2 1.4814(14) . ?
N1 C9 1.5051(13) . ?
N2 C10 1.5034(12) . ?
C1 C2 1.5182(16) . ?
C1 C8 1.5311(14) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.5068(13) . ?
C3 C10 1.5440(13) . ?
C3 H3 0.9800 . ?
C4 C5 1.3928(15) . ?
C4 C11 1.3942(14) . ?
C5 C6 1.3902(15) . ?
C5 H5 0.9300 . ?
C6 C7 1.3878(16) . ?
C6 H6 0.9300 . ?
C7 C12 1.3864(17) . ?
C7 H7 0.9300 . ?
C8 C9 1.5343(14) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.5218(13) . ?
C9 H9 0.9800 . ?
C10 H10 0.9800 . ?
C11 C12 1.3921(15) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 O1 N1 107.32(7) . . ?
O1 N1 C2 109.78(8) . . ?
O1 N1 C9 106.22(7) . . ?
C2 N1 C9 106.82(8) . . ?
O2 N2 O3 124.09(9) . . ?
O2 N2 C10 119.30(9) . . ?
O3 N2 C10 116.59(9) . . ?
C2 C1 C8 101.69(8) . . ?
C2 C1 H1A 111.4 . . ?
C8 C1 H1A 111.4 . . ?
C2 C1 H1B 111.4 . . ?
C8 C1 H1B 111.4 . . ?
H1A C1 H1B 109.3 . . ?
N1 C2 C1 102.47(8) . . ?
N1 C2 H2A 111.3 . . ?
C1 C2 H2A 111.3 . . ?
N1 C2 H2B 111.3 . . ?
C1 C2 H2B 111.3 . . ?
H2A C2 H2B 109.2 . . ?
O1 C3 C4 109.38(8) . . ?
O1 C3 C10 102.97(7) . . ?
C4 C3 C10 118.91(8) . . ?
O1 C3 H3 108.4 . . ?
C4 C3 H3 108.4 . . ?
C10 C3 H3 108.4 . . ?
C5 C4 C11 119.21(9) . . ?
C5 C4 C3 121.32(9) . . ?
C11 C4 C3 119.43(9) . . ?
C6 C5 C4 120.31(10) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C7 C6 C5 120.29(10) . . ?
C7 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C12 C7 C6 119.67(10) . . ?
C12 C7 H7 120.2 . . ?
C6 C7 H7 120.2 . . ?
C1 C8 C9 102.34(8) . . ?
C1 C8 H8A 111.3 . . ?
C9 C8 H8A 111.3 . . ?
C1 C8 H8B 111.3 . . ?
C9 C8 H8B 111.3 . . ?
H8A C8 H8B 109.2 . . ?
N1 C9 C10 105.76(8) . . ?
N1 C9 C8 106.02(8) . . ?
C10 C9 C8 115.30(8) . . ?
N1 C9 H9 109.8 . . ?
C10 C9 H9 109.8 . . ?
C8 C9 H9 109.8 . . ?
N2 C10 C9 112.03(8) . . ?
N2 C10 C3 109.13(8) . . ?
C9 C10 C3 102.00(7) . . ?
N2 C10 H10 111.1 . . ?
C9 C10 H10 111.1 . . ?
C3 C10 H10 111.1 . . ?
C12 C11 C4 120.27(10) . . ?
C12 C11 H11 119.9 . . ?
C4 C11 H11 119.9 . . ?
C7 C12 C11 120.25(10) . . ?
C7 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.54
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.343
_refine_diff_density_min         -0.318
_refine_diff_density_rms         0.065
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_12_10again
_database_code_depnum_ccdc_archive 'CCDC 1006038'
_audit_update_record             
;
2014-05-30 deposited with the CCDC.
2016-11-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H17 N O5'
_chemical_formula_weight         291.30

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   P2(1)/c

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

_cell_length_a                   9.1248(8)
_cell_length_b                   32.242(3)
_cell_length_c                   9.4579(9)
_cell_angle_alpha                90.13
_cell_angle_beta                 90.000(6)
_cell_angle_gamma                90.00
_cell_volume                     2782.5(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    8170
_cell_measurement_theta_min      2.50
_cell_measurement_theta_max      26.71

_exptl_crystal_description       NEEDLE
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1232
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9672
_exptl_absorpt_correction_T_max  0.9885
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            47642
_diffrn_reflns_av_R_equivalents  0.0773
_diffrn_reflns_av_sigmaI/netI    0.0560
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -42
_diffrn_reflns_limit_k_max       40
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.26
_diffrn_reflns_theta_max         27.64
_reflns_number_total             6429
_reflns_number_gt                4984
_reflns_threshold_expression     >2sigma(I)

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

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0731P)²+0.4780P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6429
_refine_ls_number_parameters     384
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0681
_refine_ls_R_factor_gt           0.0473
_refine_ls_wR_factor_ref         0.1356
_refine_ls_wR_factor_gt          0.1190
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_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
N1A N 0.9357(2) 0.15550(6) 0.7238(2) 0.0229(5) Uani 1 1 d . . .
O1A O 0.96062(19) 0.17816(5) 0.85472(19) 0.0263(4) Uani 1 1 d . . .
O2A O 0.7533(2) 0.23647(5) 0.9420(2) 0.0334(5) Uani 1 1 d . . .
O3A O 0.6706(2) 0.19237(5) 1.1075(2) 0.0306(4) Uani 1 1 d . . .
O4A O 0.8041(2) 0.08398(5) 1.0837(2) 0.0276(4) Uani 1 1 d . . .
O5A O 0.5846(2) 0.08554(5) 0.97478(19) 0.0246(4) Uani 1 1 d . . .
C1A C 0.7886(3) 0.09408(7) 0.6554(3) 0.0207(5) Uani 1 1 d . . .
C2A C 0.7461(3) 0.05328(8) 0.6789(3) 0.0233(5) Uani 1 1 d . . .
H2A H 0.7681 0.0406 0.7645 0.028 Uiso 1 1 calc R . .
C3A C 0.6707(3) 0.03133(8) 0.5748(3) 0.0261(6) Uani 1 1 d . . .
H3A H 0.6420 0.0041 0.5907 0.031 Uiso 1 1 calc R . .
C4A C 0.6389(3) 0.05037(8) 0.4482(3) 0.0266(6) Uani 1 1 d . . .
H4A H 0.5882 0.0358 0.3787 0.032 Uiso 1 1 calc R . .
C5A C 0.6817(3) 0.09089(8) 0.4234(3) 0.0244(6) Uani 1 1 d . . .
H5A H 0.6599 0.1033 0.3372 0.029 Uiso 1 1 calc R . .
C6A C 0.7572(3) 0.11324(7) 0.5262(3) 0.0212(5) Uani 1 1 d . . .
C7A C 0.8115(3) 0.15671(8) 0.4987(3) 0.0249(5) Uani 1 1 d . . .
H7A1 H 0.7404 0.1713 0.4411 0.030 Uiso 1 1 calc R . .
H7A2 H 0.9028 0.1554 0.4463 0.030 Uiso 1 1 calc R . .
C8A C 0.8358(3) 0.18056(7) 0.6358(3) 0.0236(5) Uani 1 1 d . . .
H8A1 H 0.8790 0.2074 0.6163 0.028 Uiso 1 1 calc R . .
H8A2 H 0.7434 0.1848 0.6843 0.028 Uiso 1 1 calc R . .
C9A C 0.8514(3) 0.16665(7) 0.9574(3) 0.0223(5) Uani 1 1 d . . .
H9A H 0.9005 0.1561 1.0423 0.027 Uiso 1 1 calc R . .
C10A C 0.7603(3) 0.13199(7) 0.8923(3) 0.0207(5) Uani 1 1 d . . .
H10A H 0.6705 0.1435 0.8511 0.025 Uiso 1 1 calc R . .
C11A C 0.8650(3) 0.11717(7) 0.7728(3) 0.0197(5) Uani 1 1 d . . .
H11A H 0.9399 0.0991 0.8139 0.024 Uiso 1 1 calc R . .
C12A C 0.7224(3) 0.09826(8) 0.9960(3) 0.0224(5) Uani 1 1 d . . .
C13A C 0.5314(3) 0.05269(8) 1.0653(3) 0.0288(6) Uani 1 1 d . . .
H13A H 0.6079 0.0327 1.0798 0.043 Uiso 1 1 calc R . .
H13B H 0.4489 0.0394 1.0214 0.043 Uiso 1 1 calc R . .
H13C H 0.5022 0.0642 1.1547 0.043 Uiso 1 1 calc R . .
C14A C 0.7556(3) 0.20345(7) 0.9981(3) 0.0229(5) Uani 1 1 d . . .
C15A C 0.5678(3) 0.22354(8) 1.1585(3) 0.0311(6) Uani 1 1 d . . .
H15A H 0.6179 0.2425 1.2203 0.047 Uiso 1 1 calc R . .
H15B H 0.4899 0.2102 1.2092 0.047 Uiso 1 1 calc R . .
H15C H 0.5280 0.2385 1.0797 0.047 Uiso 1 1 calc R . .
N1B N 0.4333(2) 0.15449(6) 0.7135(2) 0.0225(5) Uani 1 1 d . . .
O1B O 0.45967(19) 0.17710(5) 0.58286(19) 0.0247(4) Uani 1 1 d . . .
O2B O 0.2556(2) 0.23550(5) 0.4947(2) 0.0337(5) Uani 1 1 d . . .
O3B O 0.1734(2) 0.19153(5) 0.3282(2) 0.0303(4) Uani 1 1 d . . .
O4B O 0.3048(2) 0.08300(6) 0.3522(2) 0.0283(4) Uani 1 1 d . . .
O5B O 0.0863(2) 0.08366(5) 0.46294(19) 0.0250(4) Uani 1 1 d . . .
C1B C 0.2879(3) 0.09217(7) 0.7791(3) 0.0199(5) Uani 1 1 d . . .
C2B C 0.2479(3) 0.05123(7) 0.7551(3) 0.0224(5) Uani 1 1 d . . .
H2B H 0.2726 0.0386 0.6698 0.027 Uiso 1 1 calc R . .
C3B C 0.1715(3) 0.02883(8) 0.8565(3) 0.0249(6) Uani 1 1 d . . .
H3B H 0.1453 0.0014 0.8393 0.030 Uiso 1 1 calc R . .
C4B C 0.1349(3) 0.04763(8) 0.9831(3) 0.0261(6) Uani 1 1 d . . .
H4B H 0.0824 0.0330 1.0510 0.031 Uiso 1 1 calc R . .
C5B C 0.1764(3) 0.08838(8) 1.0088(3) 0.0247(6) Uani 1 1 d . . .
H5B H 0.1521 0.1007 1.0946 0.030 Uiso 1 1 calc R . .
C6B C 0.2539(3) 0.11117(8) 0.9085(3) 0.0224(5) Uani 1 1 d . . .
C7B C 0.3048(3) 0.15446(7) 0.9378(3) 0.0234(5) Uani 1 1 d . . .
H7B1 H 0.3942 0.1535 0.9931 0.028 Uiso 1 1 calc R . .
H7B2 H 0.2311 0.1688 0.9934 0.028 Uiso 1 1 calc R . .
C8B C 0.3330(3) 0.17861(8) 0.8030(3) 0.0242(6) Uani 1 1 d . . .
H8B1 H 0.2415 0.1834 0.7535 0.029 Uiso 1 1 calc R . .
H8B2 H 0.3762 0.2053 0.8255 0.029 Uiso 1 1 calc R . .
C9B C 0.3527(3) 0.16580(8) 0.4801(3) 0.0230(5) Uani 1 1 d . . .
H9B H 0.4027 0.1553 0.3956 0.028 Uiso 1 1 calc R . .
C10B C 0.2597(3) 0.13060(7) 0.5443(2) 0.0195(5) Uani 1 1 d . . .
H10B H 0.1697 0.1420 0.5854 0.023 Uiso 1 1 calc R . .
C11B C 0.3651(3) 0.11595(7) 0.6641(3) 0.0206(5) Uani 1 1 d . . .
H11B H 0.4410 0.0982 0.6226 0.025 Uiso 1 1 calc R . .
C12B C 0.2227(3) 0.09689(7) 0.4403(3) 0.0195(5) Uani 1 1 d . . .
C13B C 0.0339(3) 0.05075(8) 0.3727(3) 0.0266(6) Uani 1 1 d . . .
H13D H -0.0030 0.0623 0.2863 0.040 Uiso 1 1 calc R . .
H13E H -0.0432 0.0360 0.4199 0.040 Uiso 1 1 calc R . .
H13F H 0.1129 0.0321 0.3519 0.040 Uiso 1 1 calc R . .
C14B C 0.2572(3) 0.20242(8) 0.4387(3) 0.0238(5) Uani 1 1 d . . .
C15B C 0.0734(3) 0.22291(8) 0.2768(3) 0.0314(6) Uani 1 1 d . . .
H15D H 0.0122 0.2323 0.3531 0.047 Uiso 1 1 calc R . .
H15E H 0.0133 0.2114 0.2033 0.047 Uiso 1 1 calc R . .
H15F H 0.1282 0.2459 0.2401 0.047 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1A O1A 1.454(3) . ?
N1A C11A 1.470(3) . ?
N1A C8A 1.476(3) . ?
O1A C9A 1.441(3) . ?
O2A C14A 1.191(3) . ?
O3A C14A 1.342(3) . ?
O3A C15A 1.456(3) . ?
O4A C12A 1.208(3) . ?
O5A C12A 1.337(3) . ?
O5A C13A 1.447(3) . ?
C1A C2A 1.390(3) . ?
C1A C6A 1.400(3) . ?
C1A C11A 1.506(3) . ?
C2A C3A 1.393(4) . ?
C2A H2A 0.9300 . ?
C3A C4A 1.378(4) . ?
C3A H3A 0.9300 . ?
C4A C5A 1.384(4) . ?
C4A H4A 0.9300 . ?
C5A C6A 1.391(4) . ?
C5A H5A 0.9300 . ?
C6A C7A 1.510(3) . ?
C7A C8A 1.523(4) . ?
C7A H7A1 0.9700 . ?
C7A H7A2 0.9700 . ?
C8A H8A1 0.9700 . ?
C8A H8A2 0.9700 . ?
C9A C10A 1.522(3) . ?
C9A C14A 1.523(3) . ?
C9A H9A 0.9800 . ?
C10A C12A 1.506(3) . ?
C10A C11A 1.555(3) . ?
C10A H10A 0.9800 . ?
C11A H11A 0.9800 . ?
C13A H13A 0.9600 . ?
C13A H13B 0.9600 . ?
C13A H13C 0.9600 . ?
C15A H15A 0.9600 . ?
C15A H15B 0.9600 . ?
C15A H15C 0.9600 . ?
N1B O1B 1.456(3) . ?
N1B C11B 1.465(3) . ?
N1B C8B 1.468(3) . ?
O1B C9B 1.425(3) . ?
O2B C14B 1.190(3) . ?
O3B C14B 1.341(3) . ?
O3B C15B 1.447(3) . ?
O4B C12B 1.206(3) . ?
O5B C12B 1.334(3) . ?
O5B C13B 1.441(3) . ?
C1B C2B 1.388(3) . ?
C1B C6B 1.402(3) . ?
C1B C11B 1.507(3) . ?
C2B C3B 1.389(4) . ?
C2B H2B 0.9300 . ?
C3B C4B 1.382(4) . ?
C3B H3B 0.9300 . ?
C4B C5B 1.388(4) . ?
C4B H4B 0.9300 . ?
C5B C6B 1.394(4) . ?
C5B H5B 0.9300 . ?
C6B C7B 1.496(3) . ?
C7B C8B 1.517(4) . ?
C7B H7B1 0.9700 . ?
C7B H7B2 0.9700 . ?
C8B H8B1 0.9700 . ?
C8B H8B2 0.9700 . ?
C9B C14B 1.519(3) . ?
C9B C10B 1.543(3) . ?
C9B H9B 0.9800 . ?
C10B C12B 1.502(3) . ?
C10B C11B 1.560(3) . ?
C10B H10B 0.9800 . ?
C11B H11B 0.9800 . ?
C13B H13D 0.9600 . ?
C13B H13E 0.9600 . ?
C13B H13F 0.9600 . ?
C15B H15D 0.9600 . ?
C15B H15E 0.9600 . ?
C15B H15F 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1A N1A C11A 102.81(17) . . ?
O1A N1A C8A 107.60(18) . . ?
C11A N1A C8A 111.6(2) . . ?
C9A O1A N1A 109.66(17) . . ?
C14A O3A C15A 116.3(2) . . ?
C12A O5A C13A 116.8(2) . . ?
C2A C1A C6A 120.2(2) . . ?
C2A C1A C11A 118.5(2) . . ?
C6A C1A C11A 121.3(2) . . ?
C1A C2A C3A 120.3(2) . . ?
C1A C2A H2A 119.9 . . ?
C3A C2A H2A 119.9 . . ?
C4A C3A C2A 119.4(2) . . ?
C4A C3A H3A 120.3 . . ?
C2A C3A H3A 120.3 . . ?
C3A C4A C5A 120.7(2) . . ?
C3A C4A H4A 119.7 . . ?
C5A C4A H4A 119.7 . . ?
C4A C5A C6A 120.6(2) . . ?
C4A C5A H5A 119.7 . . ?
C6A C5A H5A 119.7 . . ?
C5A C6A C1A 118.9(2) . . ?
C5A C6A C7A 121.4(2) . . ?
C1A C6A C7A 119.7(2) . . ?
C6A C7A C8A 111.6(2) . . ?
C6A C7A H7A1 109.3 . . ?
C8A C7A H7A1 109.3 . . ?
C6A C7A H7A2 109.3 . . ?
C8A C7A H7A2 109.3 . . ?
H7A1 C7A H7A2 108.0 . . ?
N1A C8A C7A 107.1(2) . . ?
N1A C8A H8A1 110.3 . . ?
C7A C8A H8A1 110.3 . . ?
N1A C8A H8A2 110.3 . . ?
C7A C8A H8A2 110.3 . . ?
H8A1 C8A H8A2 108.5 . . ?
O1A C9A C10A 107.2(2) . . ?
O1A C9A C14A 111.5(2) . . ?
C10A C9A C14A 111.1(2) . . ?
O1A C9A H9A 109.0 . . ?
C10A C9A H9A 109.0 . . ?
C14A C9A H9A 109.0 . . ?
C12A C10A C9A 113.1(2) . . ?
C12A C10A C11A 113.2(2) . . ?
C9A C10A C11A 100.50(19) . . ?
C12A C10A H10A 109.9 . . ?
C9A C10A H10A 109.9 . . ?
C11A C10A H10A 109.9 . . ?
N1A C11A C1A 112.7(2) . . ?
N1A C11A C10A 103.98(18) . . ?
C1A C11A C10A 113.7(2) . . ?
N1A C11A H11A 108.8 . . ?
C1A C11A H11A 108.8 . . ?
C10A C11A H11A 108.8 . . ?
O4A C12A O5A 124.5(2) . . ?
O4A C12A C10A 125.6(2) . . ?
O5A C12A C10A 109.9(2) . . ?
O5A C13A H13A 109.5 . . ?
O5A C13A H13B 109.5 . . ?
H13A C13A H13B 109.5 . . ?
O5A C13A H13C 109.5 . . ?
H13A C13A H13C 109.5 . . ?
H13B C13A H13C 109.5 . . ?
O2A C14A O3A 125.0(2) . . ?
O2A C14A C9A 126.5(2) . . ?
O3A C14A C9A 108.6(2) . . ?
O3A C15A H15A 109.5 . . ?
O3A C15A H15B 109.5 . . ?
H15A C15A H15B 109.5 . . ?
O3A C15A H15C 109.5 . . ?
H15A C15A H15C 109.5 . . ?
H15B C15A H15C 109.5 . . ?
O1B N1B C11B 103.01(17) . . ?
O1B N1B C8B 109.06(18) . . ?
C11B N1B C8B 111.5(2) . . ?
C9B O1B N1B 109.78(17) . . ?
C14B O3B C15B 116.0(2) . . ?
C12B O5B C13B 116.7(2) . . ?
C2B C1B C6B 119.9(2) . . ?
C2B C1B C11B 119.3(2) . . ?
C6B C1B C11B 120.8(2) . . ?
C1B C2B C3B 121.0(2) . . ?
C1B C2B H2B 119.5 . . ?
C3B C2B H2B 119.5 . . ?
C4B C3B C2B 119.5(2) . . ?
C4B C3B H3B 120.3 . . ?
C2B C3B H3B 120.3 . . ?
C3B C4B C5B 119.9(3) . . ?
C3B C4B H4B 120.1 . . ?
C5B C4B H4B 120.1 . . ?
C4B C5B C6B 121.3(2) . . ?
C4B C5B H5B 119.3 . . ?
C6B C5B H5B 119.3 . . ?
C5B C6B C1B 118.4(2) . . ?
C5B C6B C7B 121.7(2) . . ?
C1B C6B C7B 119.9(2) . . ?
C6B C7B C8B 112.2(2) . . ?
C6B C7B H7B1 109.2 . . ?
C8B C7B H7B1 109.2 . . ?
C6B C7B H7B2 109.2 . . ?
C8B C7B H7B2 109.2 . . ?
H7B1 C7B H7B2 107.9 . . ?
N1B C8B C7B 108.5(2) . . ?
N1B C8B H8B1 110.0 . . ?
C7B C8B H8B1 110.0 . . ?
N1B C8B H8B2 110.0 . . ?
C7B C8B H8B2 110.0 . . ?
H8B1 C8B H8B2 108.4 . . ?
O1B C9B C14B 111.8(2) . . ?
O1B C9B C10B 107.17(19) . . ?
C14B C9B C10B 111.0(2) . . ?
O1B C9B H9B 108.9 . . ?
C14B C9B H9B 108.9 . . ?
C10B C9B H9B 108.9 . . ?
C12B C10B C9B 113.4(2) . . ?
C12B C10B C11B 113.22(19) . . ?
C9B C10B C11B 99.88(19) . . ?
C12B C10B H10B 110.0 . . ?
C9B C10B H10B 110.0 . . ?
C11B C10B H10B 110.0 . . ?
N1B C11B C1B 113.6(2) . . ?
N1B C11B C10B 103.64(18) . . ?
C1B C11B C10B 113.1(2) . . ?
N1B C11B H11B 108.8 . . ?
C1B C11B H11B 108.8 . . ?
C10B C11B H11B 108.8 . . ?
O4B C12B O5B 124.9(2) . . ?
O4B C12B C10B 125.4(2) . . ?
O5B C12B C10B 109.6(2) . . ?
O5B C13B H13D 109.5 . . ?
O5B C13B H13E 109.5 . . ?
H13D C13B H13E 109.5 . . ?
O5B C13B H13F 109.5 . . ?
H13D C13B H13F 109.5 . . ?
H13E C13B H13F 109.5 . . ?
O2B C14B O3B 125.0(2) . . ?
O2B C14B C9B 126.0(2) . . ?
O3B C14B C9B 109.0(2) . . ?
O3B C15B H15D 109.5 . . ?
O3B C15B H15E 109.5 . . ?
H15D C15B H15E 109.5 . . ?
O3B C15B H15F 109.5 . . ?
H15D C15B H15F 109.5 . . ?
H15E C15B H15F 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        27.64
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.490
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.060
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_jrs15_2_0m
_database_code_depnum_ccdc_archive 'CCDC 1006039'
_audit_update_record             
;
2014-05-30 deposited with the CCDC.
2016-11-01 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 H14 N2 O3'
_chemical_formula_weight         258.27

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/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                   6.8159(2)
_cell_length_b                   26.7835(7)
_cell_length_c                   7.0628(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 114.2140(10)
_cell_angle_gamma                90.00
_cell_volume                     1175.90(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9909
_cell_measurement_theta_min      3.04
_cell_measurement_theta_max      27.46

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.459
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             544
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9654
_exptl_absorpt_correction_T_max  0.9958
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20165
_diffrn_reflns_av_R_equivalents  0.0225
_diffrn_reflns_av_sigmaI/netI    0.0115
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         1.52
_diffrn_reflns_theta_max         27.48
_reflns_number_total             2686
_reflns_number_gt                2480
_reflns_threshold_expression     >2sigma(I)

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

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0652P)²+0.4612P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2686
_refine_ls_number_parameters     173
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0400
_refine_ls_R_factor_gt           0.0362
_refine_ls_wR_factor_ref         0.1157
_refine_ls_wR_factor_gt          0.1041
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_restrained_S_all      1.106
_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
O1 O 0.19953(15) 0.40169(3) 0.58453(15) 0.0221(2) Uani 1 1 d . . .
O2 O 0.41904(13) 0.45019(3) 0.33767(13) 0.0166(2) Uani 1 1 d . . .
O3 O 0.55151(17) 0.28393(3) 0.37779(16) 0.0264(2) Uani 1 1 d . . .
N1 N 0.34161(17) 0.33519(4) 0.47711(16) 0.0166(2) Uani 1 1 d . . .
N2 N 0.52407(15) 0.44610(4) 0.19623(15) 0.0150(2) Uani 1 1 d . . .
C1 C 0.98081(19) 0.35087(5) -0.09319(18) 0.0171(2) Uani 1 1 d . . .
H1 H 1.0747 0.3418 -0.1525 0.020 Uiso 1 1 calc R . .
C2 C 0.98247(18) 0.39944(4) -0.02346(18) 0.0163(2) Uani 1 1 d . . .
H8 H 1.0763 0.4227 -0.0386 0.020 Uiso 1 1 calc R . .
C3 C 0.84490(18) 0.41385(4) 0.06920(17) 0.0142(2) Uani 1 1 d . . .
C4 C 0.70338(17) 0.37844(4) 0.08794(17) 0.0129(2) Uani 1 1 d . . .
C5 C 0.55064(17) 0.39208(4) 0.18478(17) 0.0128(2) Uani 1 1 d . . .
H5 H 0.4097 0.3777 0.0992 0.015 Uiso 1 1 calc R . .
C6 C 0.61747(18) 0.37374(4) 0.41278(17) 0.0150(2) Uani 1 1 d . . .
H6 H 0.7739 0.3724 0.4910 0.018 Uiso 1 1 calc R . .
C7 C 0.5095(2) 0.32520(4) 0.42034(18) 0.0175(3) Uani 1 1 d . . .
C8 C 0.1976(2) 0.29649(5) 0.4900(2) 0.0225(3) Uani 1 1 d . . .
H14 H 0.1542 0.2754 0.3697 0.034 Uiso 1 1 calc R . .
H3 H 0.0729 0.3117 0.4964 0.034 Uiso 1 1 calc R . .
H2 H 0.2708 0.2768 0.6126 0.034 Uiso 1 1 calc R . .
C9 C 0.33063(19) 0.38484(4) 0.52739(17) 0.0161(2) Uani 1 1 d . . .
C10 C 0.51216(18) 0.41269(4) 0.49827(18) 0.0157(2) Uani 1 1 d . . .
H13 H 0.6148 0.4272 0.6286 0.019 Uiso 1 1 calc R . .
C11 C 0.73497(19) 0.47144(4) 0.29039(19) 0.0184(3) Uani 1 1 d . . .
H11 H 0.8240 0.4559 0.4218 0.022 Uiso 1 1 calc R . .
H12 H 0.7156 0.5063 0.3156 0.022 Uiso 1 1 calc R . .
C12 C 0.84188(19) 0.46697(4) 0.13972(19) 0.0176(3) Uani 1 1 d . . .
H9 H 0.7654 0.4878 0.0195 0.021 Uiso 1 1 calc R . .
H10 H 0.9884 0.4792 0.2063 0.021 Uiso 1 1 calc R . .
C13 C 0.83909(19) 0.31578(4) -0.07453(18) 0.0169(2) Uani 1 1 d . . .
H4 H 0.8377 0.2833 -0.1215 0.020 Uiso 1 1 calc R . .
C14 C 0.69988(19) 0.32971(4) 0.01475(18) 0.0152(2) Uani 1 1 d . . .
H7 H 0.6037 0.3065 0.0260 0.018 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C9 1.2086(15) . ?
O2 N2 1.4522(12) . ?
O2 C10 1.4519(14) . ?
O3 C7 1.2103(15) . ?
N1 C7 1.3852(15) . ?
N1 C9 1.3862(15) . ?
N1 C8 1.4560(16) . ?
N2 C5 1.4645(14) . ?
N2 C11 1.4781(15) . ?
C1 C2 1.3893(17) . ?
C1 C13 1.3922(17) . ?
C1 H1 0.9300 . ?
C2 C3 1.3999(16) . ?
C2 H8 0.9300 . ?
C3 C4 1.3972(16) . ?
C3 C12 1.5103(16) . ?
C4 C14 1.4003(15) . ?
C4 C5 1.5064(15) . ?
C5 C6 1.5620(15) . ?
C5 H5 0.9800 . ?
C6 C7 1.5055(16) . ?
C6 C10 1.5242(15) . ?
C6 H6 0.9800 . ?
C8 H14 0.9600 . ?
C8 H3 0.9600 . ?
C8 H2 0.9600 . ?
C9 C10 1.5291(17) . ?
C10 H13 0.9800 . ?
C11 C12 1.5211(17) . ?
C11 H11 0.9700 . ?
C11 H12 0.9700 . ?
C12 H9 0.9700 . ?
C12 H10 0.9700 . ?
C13 C14 1.3885(16) . ?
C13 H4 0.9300 . ?
C14 H7 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 O2 C10 107.72(8) . . ?
C7 N1 C9 113.41(10) . . ?
C7 N1 C8 122.61(10) . . ?
C9 N1 C8 123.93(10) . . ?
O2 N2 C5 102.68(8) . . ?
O2 N2 C11 108.58(9) . . ?
C5 N2 C11 111.04(9) . . ?
C2 C1 C13 120.24(11) . . ?
C2 C1 H1 119.9 . . ?
C13 C1 H1 119.9 . . ?
C1 C2 C3 120.94(11) . . ?
C1 C2 H8 119.5 . . ?
C3 C2 H8 119.5 . . ?
C4 C3 C2 118.55(10) . . ?
C4 C3 C12 120.32(10) . . ?
C2 C3 C12 121.07(10) . . ?
C3 C4 C14 120.37(11) . . ?
C3 C4 C5 120.72(10) . . ?
C14 C4 C5 118.90(10) . . ?
N2 C5 C4 112.88(9) . . ?
N2 C5 C6 104.13(9) . . ?
C4 C5 C6 115.35(9) . . ?
N2 C5 H5 108.1 . . ?
C4 C5 H5 108.1 . . ?
C6 C5 H5 108.1 . . ?
C7 C6 C10 105.10(9) . . ?
C7 C6 C5 111.59(9) . . ?
C10 C6 C5 101.98(9) . . ?
C7 C6 H6 112.5 . . ?
C10 C6 H6 112.5 . . ?
C5 C6 H6 112.5 . . ?
O3 C7 N1 123.77(12) . . ?
O3 C7 C6 127.68(11) . . ?
N1 C7 C6 108.50(10) . . ?
N1 C8 H14 109.5 . . ?
N1 C8 H3 109.5 . . ?
H14 C8 H3 109.5 . . ?
N1 C8 H2 109.5 . . ?
H14 C8 H2 109.5 . . ?
H3 C8 H2 109.5 . . ?
O1 C9 N1 124.66(11) . . ?
O1 C9 C10 127.78(11) . . ?
N1 C9 C10 107.56(10) . . ?
O2 C10 C6 106.85(9) . . ?
O2 C10 C9 108.91(9) . . ?
C6 C10 C9 104.95(9) . . ?
O2 C10 H13 111.9 . . ?
C6 C10 H13 111.9 . . ?
C9 C10 H13 111.9 . . ?
N2 C11 C12 107.80(9) . . ?
N2 C11 H11 110.1 . . ?
C12 C11 H11 110.1 . . ?
N2 C11 H12 110.1 . . ?
C12 C11 H12 110.1 . . ?
H11 C11 H12 108.5 . . ?
C3 C12 C11 112.34(10) . . ?
C3 C12 H9 109.1 . . ?
C11 C12 H9 109.1 . . ?
C3 C12 H10 109.1 . . ?
C11 C12 H10 109.1 . . ?
H9 C12 H10 107.9 . . ?
C14 C13 C1 119.45(11) . . ?
C14 C13 H4 120.3 . . ?
C1 C13 H4 120.3 . . ?
C13 C14 C4 120.44(11) . . ?
C13 C14 H7 119.8 . . ?
C4 C14 H7 119.8 . . ?

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 O2 N2 C5 38.08(10) . . . . ?
C10 O2 N2 C11 -79.56(10) . . . . ?
C13 C1 C2 C3 0.95(17) . . . . ?
C1 C2 C3 C4 -0.79(16) . . . . ?
C1 C2 C3 C12 -178.27(10) . . . . ?
C2 C3 C4 C14 -0.16(16) . . . . ?
C12 C3 C4 C14 177.35(10) . . . . ?
C2 C3 C4 C5 -179.49(10) . . . . ?
C12 C3 C4 C5 -1.98(16) . . . . ?
O2 N2 C5 C4 -166.15(8) . . . . ?
C11 N2 C5 C4 -50.27(12) . . . . ?
O2 N2 C5 C6 -40.32(10) . . . . ?
C11 N2 C5 C6 75.56(11) . . . . ?
C3 C4 C5 N2 16.78(14) . . . . ?
C14 C4 C5 N2 -162.55(10) . . . . ?
C3 C4 C5 C6 -102.76(12) . . . . ?
C14 C4 C5 C6 77.90(13) . . . . ?
N2 C5 C6 C7 139.74(9) . . . . ?
C4 C5 C6 C7 -96.00(11) . . . . ?
N2 C5 C6 C10 28.00(11) . . . . ?
C4 C5 C6 C10 152.26(9) . . . . ?
C9 N1 C7 O3 177.34(12) . . . . ?
C8 N1 C7 O3 -0.30(19) . . . . ?
C9 N1 C7 C6 -5.14(13) . . . . ?
C8 N1 C7 C6 177.21(10) . . . . ?
C10 C6 C7 O3 -175.61(12) . . . . ?
C5 C6 C7 O3 74.63(16) . . . . ?
C10 C6 C7 N1 7.00(12) . . . . ?
C5 C6 C7 N1 -102.75(11) . . . . ?
C7 N1 C9 O1 -178.66(11) . . . . ?
C8 N1 C9 O1 -1.05(19) . . . . ?
C7 N1 C9 C10 0.97(13) . . . . ?
C8 N1 C9 C10 178.58(10) . . . . ?
N2 O2 C10 C6 -19.85(11) . . . . ?
N2 O2 C10 C9 -132.73(9) . . . . ?
C7 C6 C10 O2 -121.76(10) . . . . ?
C5 C6 C10 O2 -5.21(11) . . . . ?
C7 C6 C10 C9 -6.20(11) . . . . ?
C5 C6 C10 C9 110.34(10) . . . . ?
O1 C9 C10 O2 -62.77(15) . . . . ?
N1 C9 C10 O2 117.61(10) . . . . ?
O1 C9 C10 C6 -176.90(12) . . . . ?
N1 C9 C10 C6 3.49(12) . . . . ?
O2 N2 C11 C12 -179.74(8) . . . . ?
C5 N2 C11 C12 68.09(12) . . . . ?
C4 C3 C12 C11 19.59(15) . . . . ?
C2 C3 C12 C11 -162.97(10) . . . . ?
N2 C11 C12 C3 -50.96(13) . . . . ?
C2 C1 C13 C14 -0.15(17) . . . . ?
C1 C13 C14 C4 -0.79(17) . . . . ?
C3 C4 C14 C13 0.95(17) . . . . ?
C5 C4 C14 C13 -179.71(10) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.377
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.059
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_oic210a
_database_code_depnum_ccdc_archive 'CCDC 1006040'
_audit_update_record             
;
2014-05-30 deposited with the CCDC.
2016-11-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H16 N2 O3'
_chemical_formula_sum            'C15 H16 N2 O3'
_chemical_formula_weight         272.30

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   P2(1)/n
_symmetry_space_group_name_Hall  '-P 2yn'
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                   12.9691(19)
_cell_length_b                   6.6225(11)
_cell_length_c                   15.583(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.005(11)
_cell_angle_gamma                90.00
_cell_volume                     1298.6(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1148
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      22.41

_exptl_crystal_description       Block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.393
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             576
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9835
_exptl_absorpt_correction_T_max  0.9951
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11569
_diffrn_reflns_av_R_equivalents  0.0846
_diffrn_reflns_av_sigmaI/netI    0.0860
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.24
_diffrn_reflns_theta_max         27.54
_reflns_number_total             2984
_reflns_number_gt                1837
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1031P)²+1.3003P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2984
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1214
_refine_ls_R_factor_gt           0.0715
_refine_ls_wR_factor_ref         0.2195
_refine_ls_wR_factor_gt          0.1899
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.67906(18) 0.6034(4) 0.44441(16) 0.0285(6) Uani 1 1 d . . .
O2 O 0.48721(19) 0.3368(3) 0.38955(16) 0.0268(6) Uani 1 1 d . . .
O3 O 0.47529(18) 0.8296(3) 0.18306(15) 0.0234(6) Uani 1 1 d . . .
N1 N 0.45397(19) 0.5691(4) 0.27520(17) 0.0175(6) Uani 1 1 d . . .
N2 N 0.7206(2) 0.6074(4) 0.36453(19) 0.0257(7) Uani 1 1 d . . .
C1 C 0.4972(2) 0.7526(5) 0.2553(2) 0.0184(7) Uani 1 1 d . . .
C2 C 0.5751(2) 0.8286(5) 0.3376(2) 0.0202(7) Uani 1 1 d . . .
H2 H 0.5564 0.9665 0.3551 0.024 Uiso 1 1 calc R . .
C3 C 0.6929(3) 0.8148(5) 0.3314(2) 0.0245(8) Uani 1 1 d . . .
H3 H 0.6966 0.8247 0.2681 0.029 Uiso 1 1 calc R . .
C4 C 0.7600(3) 0.9819(5) 0.3854(2) 0.0284(8) Uani 1 1 d . . .
H4A H 0.7442 1.1121 0.3537 0.034 Uiso 1 1 calc R . .
H4B H 0.7416 0.9951 0.4432 0.034 Uiso 1 1 calc R . .
C5 C 0.8782(3) 0.9341(5) 0.4002(2) 0.0283(8) Uani 1 1 d . . .
H5A H 0.8974 0.9242 0.3426 0.034 Uiso 1 1 calc R . .
H5B H 0.9210 1.0434 0.4350 0.034 Uiso 1 1 calc R . .
C6 C 0.9014(3) 0.7364(6) 0.4494(3) 0.0328(9) Uani 1 1 d . . .
H6A H 0.8826 0.7466 0.5072 0.039 Uiso 1 1 calc R . .
H6B H 0.9781 0.7047 0.4604 0.039 Uiso 1 1 calc R . .
C7 C 0.8361(3) 0.5694(5) 0.3938(3) 0.0311(9) Uani 1 1 d . . .
H7A H 0.8640 0.5474 0.3408 0.037 Uiso 1 1 calc R . .
H7B H 0.8471 0.4428 0.4287 0.037 Uiso 1 1 calc R . .
C8 C 0.5731(2) 0.6706(5) 0.4089(2) 0.0212(7) Uani 1 1 d . . .
H8 H 0.5425 0.7293 0.4564 0.025 Uiso 1 1 calc R . .
C9 C 0.5020(2) 0.5000(5) 0.3604(2) 0.0199(7) Uani 1 1 d . . .
C10 C 0.3710(2) 0.4653(5) 0.2125(2) 0.0177(7) Uani 1 1 d . . .
C11 C 0.3887(2) 0.2736(5) 0.1830(2) 0.0184(7) Uani 1 1 d . . .
H11 H 0.4550 0.2081 0.2047 0.022 Uiso 1 1 calc R . .
C12 C 0.3076(3) 0.1788(5) 0.1212(2) 0.0216(7) Uani 1 1 d . . .
H12 H 0.3188 0.0477 0.1004 0.026 Uiso 1 1 calc R . .
C13 C 0.2108(3) 0.2741(5) 0.0897(2) 0.0215(7) Uani 1 1 d . . .
H13 H 0.1559 0.2085 0.0475 0.026 Uiso 1 1 calc R . .
C14 C 0.1940(3) 0.4660(5) 0.1200(2) 0.0238(7) Uani 1 1 d . . .
H14 H 0.1276 0.5313 0.0984 0.029 Uiso 1 1 calc R . .
C15 C 0.2743(2) 0.5623(5) 0.1818(2) 0.0221(7) Uani 1 1 d . . .
H15 H 0.2630 0.6932 0.2028 0.027 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C8 1.423(4) . ?
O1 N2 1.471(4) . ?
O2 C9 1.205(4) . ?
O3 C1 1.205(4) . ?
N1 C9 1.400(4) . ?
N1 C1 1.404(4) . ?
N1 C10 1.440(4) . ?
N2 C7 1.478(4) . ?
N2 C3 1.481(4) . ?
C1 C2 1.514(4) . ?
C2 C8 1.531(5) . ?
C2 C3 1.556(4) . ?
C2 H2 1.0000 . ?
C3 C4 1.528(5) . ?
C3 H3 1.0000 . ?
C4 C5 1.527(5) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.510(5) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.528(5) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.536(4) . ?
C8 H8 1.0000 . ?
C10 C15 1.387(4) . ?
C10 C11 1.389(4) . ?
C11 C12 1.392(5) . ?
C11 H11 0.9500 . ?
C12 C13 1.384(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.391(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.390(4) . ?
C14 H14 0.9500 . ?
C15 H15 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
C8 O1 N2 100.5(2) . . ?
C9 N1 C1 112.5(3) . . ?
C9 N1 C10 125.1(3) . . ?
C1 N1 C10 122.4(3) . . ?
O1 N2 C7 106.7(3) . . ?
O1 N2 C3 101.8(2) . . ?
C7 N2 C3 114.1(3) . . ?
O3 C1 N1 123.8(3) . . ?
O3 C1 C2 127.4(3) . . ?
N1 C1 C2 108.7(3) . . ?
C1 C2 C8 105.2(2) . . ?
C1 C2 C3 113.1(3) . . ?
C8 C2 C3 101.2(2) . . ?
C1 C2 H2 112.2 . . ?
C8 C2 H2 112.2 . . ?
C3 C2 H2 112.2 . . ?
N2 C3 C4 115.0(3) . . ?
N2 C3 C2 101.0(2) . . ?
C4 C3 C2 111.1(3) . . ?
N2 C3 H3 109.8 . . ?
C4 C3 H3 109.8 . . ?
C2 C3 H3 109.8 . . ?
C5 C4 C3 110.5(3) . . ?
C5 C4 H4A 109.6 . . ?
C3 C4 H4A 109.6 . . ?
C5 C4 H4B 109.6 . . ?
C3 C4 H4B 109.6 . . ?
H4A C4 H4B 108.1 . . ?
C6 C5 C4 109.0(3) . . ?
C6 C5 H5A 109.9 . . ?
C4 C5 H5A 109.9 . . ?
C6 C5 H5B 109.9 . . ?
C4 C5 H5B 109.9 . . ?
H5A C5 H5B 108.3 . . ?
C5 C6 C7 109.0(3) . . ?
C5 C6 H6A 109.9 . . ?
C7 C6 H6A 109.9 . . ?
C5 C6 H6B 109.9 . . ?
C7 C6 H6B 109.9 . . ?
H6A C6 H6B 108.3 . . ?
N2 C7 C6 115.6(3) . . ?
N2 C7 H7A 108.4 . . ?
C6 C7 H7A 108.4 . . ?
N2 C7 H7B 108.4 . . ?
C6 C7 H7B 108.4 . . ?
H7A C7 H7B 107.4 . . ?
O1 C8 C2 108.1(2) . . ?
O1 C8 C9 111.7(3) . . ?
C2 C8 C9 105.1(3) . . ?
O1 C8 H8 110.6 . . ?
C2 C8 H8 110.6 . . ?
C9 C8 H8 110.6 . . ?
O2 C9 N1 125.1(3) . . ?
O2 C9 C8 127.3(3) . . ?
N1 C9 C8 107.6(3) . . ?
C15 C10 C11 121.1(3) . . ?
C15 C10 N1 118.5(3) . . ?
C11 C10 N1 120.3(3) . . ?
C10 C11 C12 119.0(3) . . ?
C10 C11 H11 120.5 . . ?
C12 C11 H11 120.5 . . ?
C13 C12 C11 120.5(3) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C12 C13 C14 120.0(3) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
C15 C14 C13 120.1(3) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C10 C15 C14 119.3(3) . . ?
C10 C15 H15 120.3 . . ?
C14 C15 H15 120.3 . . ?

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
C8 O1 N2 C7 171.8(2) . . . . ?
C8 O1 N2 C3 52.0(3) . . . . ?
C9 N1 C1 O3 172.5(3) . . . . ?
C10 N1 C1 O3 -6.3(5) . . . . ?
C9 N1 C1 C2 -6.1(3) . . . . ?
C10 N1 C1 C2 175.2(3) . . . . ?
O3 C1 C2 C8 -178.8(3) . . . . ?
N1 C1 C2 C8 -0.3(3) . . . . ?
O3 C1 C2 C3 -69.2(4) . . . . ?
N1 C1 C2 C3 109.3(3) . . . . ?
O1 N2 C3 C4 72.7(3) . . . . ?
C7 N2 C3 C4 -41.7(4) . . . . ?
O1 N2 C3 C2 -46.9(3) . . . . ?
C7 N2 C3 C2 -161.4(3) . . . . ?
C1 C2 C3 N2 -88.0(3) . . . . ?
C8 C2 C3 N2 24.1(3) . . . . ?
C1 C2 C3 C4 149.6(3) . . . . ?
C8 C2 C3 C4 -98.3(3) . . . . ?
N2 C3 C4 C5 50.3(4) . . . . ?
C2 C3 C4 C5 164.2(3) . . . . ?
C3 C4 C5 C6 -59.8(4) . . . . ?
C4 C5 C6 C7 60.6(4) . . . . ?
O1 N2 C7 C6 -67.9(4) . . . . ?
C3 N2 C7 C6 43.6(4) . . . . ?
C5 C6 C7 N2 -53.5(4) . . . . ?
N2 O1 C8 C2 -35.9(3) . . . . ?
N2 O1 C8 C9 79.2(3) . . . . ?
C1 C2 C8 O1 125.2(3) . . . . ?
C3 C2 C8 O1 7.2(3) . . . . ?
C1 C2 C8 C9 5.8(3) . . . . ?
C3 C2 C8 C9 -112.1(3) . . . . ?
C1 N1 C9 O2 -171.6(3) . . . . ?
C10 N1 C9 O2 7.1(5) . . . . ?
C1 N1 C9 C8 9.9(3) . . . . ?
C10 N1 C9 C8 -171.4(3) . . . . ?
O1 C8 C9 O2 55.1(4) . . . . ?
C2 C8 C9 O2 172.1(3) . . . . ?
O1 C8 C9 N1 -126.4(3) . . . . ?
C2 C8 C9 N1 -9.5(3) . . . . ?
C9 N1 C10 C15 120.2(3) . . . . ?
C1 N1 C10 C15 -61.2(4) . . . . ?
C9 N1 C10 C11 -60.6(4) . . . . ?
C1 N1 C10 C11 117.9(3) . . . . ?
C15 C10 C11 C12 0.4(5) . . . . ?
N1 C10 C11 C12 -178.8(3) . . . . ?
C10 C11 C12 C13 -0.1(5) . . . . ?
C11 C12 C13 C14 -0.1(5) . . . . ?
C12 C13 C14 C15 0.0(5) . . . . ?
C11 C10 C15 C14 -0.4(5) . . . . ?
N1 C10 C15 C14 178.7(3) . . . . ?
C13 C14 C15 C10 0.2(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        27.54
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.760
_refine_diff_density_min         -0.475
_refine_diff_density_rms         0.101
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_oic241_0m
_database_code_depnum_ccdc_archive 'CCDC 1006041'
_audit_update_record             
;
2014-05-30 deposited with the CCDC.
2016-11-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H20 N2 O5'
_chemical_formula_sum            'C21 H20 N2 O5'
_chemical_formula_weight         380.39

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c
_symmetry_space_group_name_Hall  '-P 2ybc'
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                   10.6709(10)
_cell_length_b                   7.6760(7)
_cell_length_c                   22.1886(18)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.635(4)
_cell_angle_gamma                90.00
_cell_volume                     1801.4(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    97(2)
_cell_measurement_reflns_used    9868
_cell_measurement_theta_min      2.81
_cell_measurement_theta_max      27.36

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.35
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             800
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9578
_exptl_absorpt_correction_T_max  0.9654
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      97(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            33725
_diffrn_reflns_av_R_equivalents  0.0718
_diffrn_reflns_av_sigmaI/netI    0.0378
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         1.85
_diffrn_reflns_theta_max         27.55
_reflns_number_total             4133
_reflns_number_gt                3534
_reflns_threshold_expression     >2sigma(I)

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

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0591P)²+0.4954P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4133
_refine_ls_number_parameters     255
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0488
_refine_ls_R_factor_gt           0.0412
_refine_ls_wR_factor_ref         0.1142
_refine_ls_wR_factor_gt          0.1086
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.23140(9) 0.50476(13) 0.26145(4) 0.0156(2) Uani 1 1 d . . .
N2 N 0.11395(9) 0.79359(13) 0.15315(4) 0.0150(2) Uani 1 1 d . . .
O1 O -0.34845(8) 0.58143(11) -0.05691(4) 0.0207(2) Uani 1 1 d . . .
O2 O -0.24021(8) 0.28961(11) -0.00674(4) 0.0179(2) Uani 1 1 d . . .
O3 O 0.02691(8) 0.82050(11) 0.19930(4) 0.0163(2) Uani 1 1 d . . .
O4 O 0.20227(10) 0.75413(12) 0.31602(4) 0.0269(2) Uani 1 1 d . . .
O5 O 0.20692(8) 0.27979(11) 0.19268(4) 0.0205(2) Uani 1 1 d . . .
C1 C -0.19363(11) 0.45037(15) 0.01402(5) 0.0150(2) Uani 1 1 d . . .
C2 C -0.24861(11) 0.60343(16) -0.01220(5) 0.0163(3) Uani 1 1 d . . .
C3 C -0.19911(12) 0.76326(16) 0.00871(5) 0.0165(3) Uani 1 1 d . . .
H3 H -0.2356 0.8677 -0.0087 0.020 Uiso 1 1 calc R . .
C4 C -0.09643(11) 0.77286(15) 0.05499(5) 0.0148(2) Uani 1 1 d . . .
C5 C -0.04179(11) 0.61994(15) 0.07998(5) 0.0139(2) Uani 1 1 d . . .
C6 C -0.09167(11) 0.45983(15) 0.05884(5) 0.0148(2) Uani 1 1 d . . .
H6 H -0.0544 0.3553 0.0757 0.018 Uiso 1 1 calc R . .
C7 C 0.07411(11) 0.62122(15) 0.12750(5) 0.0135(2) Uani 1 1 d . . .
H7 H 0.1463 0.5684 0.1094 0.016 Uiso 1 1 calc R . .
C8 C 0.05490(11) 0.51789(15) 0.18538(5) 0.0143(2) Uani 1 1 d . . .
H8 H -0.0222 0.4426 0.1788 0.017 Uiso 1 1 calc R . .
C9 C 0.17062(11) 0.41644(15) 0.21121(5) 0.0149(2) Uani 1 1 d . . .
C10 C 0.16695(12) 0.65383(16) 0.27547(5) 0.0175(3) Uani 1 1 d . . .
C11 C 0.04261(11) 0.66168(15) 0.23184(5) 0.0158(2) Uani 1 1 d . . .
H11 H -0.0313 0.6392 0.2541 0.019 Uiso 1 1 calc R . .
C12 C 0.08911(12) 0.93568(15) 0.10904(5) 0.0174(3) Uani 1 1 d . . .
H12A H 0.1446 0.9206 0.0770 0.021 Uiso 1 1 calc R . .
H12B H 0.1122 1.0473 0.1300 0.021 Uiso 1 1 calc R . .
C13 C -0.04752(12) 0.94736(15) 0.07877(5) 0.0169(3) Uani 1 1 d . . .
H13A H -0.1013 0.9911 0.1086 0.020 Uiso 1 1 calc R . .
H13B H -0.0530 1.0316 0.0447 0.020 Uiso 1 1 calc R . .
C14 C 0.34488(11) 0.43781(15) 0.29609(5) 0.0160(3) Uani 1 1 d . . .
C15 C 0.33427(13) 0.31074(18) 0.33931(6) 0.0230(3) Uani 1 1 d . . .
H15 H 0.2534 0.2728 0.3474 0.028 Uiso 1 1 calc R . .
C16 C 0.44351(14) 0.23947(19) 0.37071(6) 0.0273(3) Uani 1 1 d . . .
H16 H 0.4376 0.1528 0.4008 0.033 Uiso 1 1 calc R . .
C17 C 0.56116(13) 0.29446(18) 0.35829(6) 0.0241(3) Uani 1 1 d . . .
H17 H 0.6357 0.2449 0.3797 0.029 Uiso 1 1 calc R . .
C18 C 0.57040(12) 0.42116(17) 0.31480(6) 0.0231(3) Uani 1 1 d . . .
H18 H 0.6512 0.4583 0.3064 0.028 Uiso 1 1 calc R . .
C19 C 0.46173(12) 0.49433(16) 0.28330(6) 0.0204(3) Uani 1 1 d . . .
H19 H 0.4676 0.5817 0.2535 0.024 Uiso 1 1 calc R . .
C20 C -0.39218(13) 0.73299(17) -0.09105(6) 0.0227(3) Uani 1 1 d . . .
H20A H -0.4250 0.8177 -0.0640 0.034 Uiso 1 1 calc R . .
H20B H -0.4596 0.7000 -0.1234 0.034 Uiso 1 1 calc R . .
H20C H -0.3219 0.7850 -0.1090 0.034 Uiso 1 1 calc R . .
C21 C -0.34840(12) 0.23970(17) 0.02126(6) 0.0221(3) Uani 1 1 d . . .
H21A H -0.3240 0.2281 0.0652 0.033 Uiso 1 1 calc R . .
H21B H -0.3809 0.1280 0.0044 0.033 Uiso 1 1 calc R . .
H21C H -0.4142 0.3289 0.0132 0.033 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C9 1.3895(15) . ?
N1 C10 1.3913(16) . ?
N1 C14 1.4401(15) . ?
N2 C12 1.4659(15) . ?
N2 C7 1.4802(14) . ?
N2 O3 1.4854(12) . ?
O1 C2 1.3665(14) . ?
O1 C20 1.4322(15) . ?
O2 C1 1.3862(13) . ?
O2 C21 1.4340(15) . ?
O3 C11 1.4154(14) . ?
O4 C10 1.2060(15) . ?
O5 C9 1.2090(14) . ?
C1 C6 1.3748(16) . ?
C1 C2 1.4044(17) . ?
C2 C3 1.3907(17) . ?
C3 C4 1.4006(17) . ?
C3 H3 0.9500 . ?
C4 C5 1.3926(16) . ?
C4 C13 1.5072(16) . ?
C5 C6 1.3955(16) . ?
C5 C7 1.5149(16) . ?
C6 H6 0.9500 . ?
C7 C8 1.5461(16) . ?
C7 H7 1.0000 . ?
C8 C9 1.5073(16) . ?
C8 C11 1.5277(16) . ?
C8 H8 1.0000 . ?
C10 C11 1.5363(17) . ?
C11 H11 1.0000 . ?
C12 C13 1.5247(17) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.3830(18) . ?
C14 C19 1.3847(17) . ?
C15 C16 1.3885(19) . ?
C15 H15 0.9500 . ?
C16 C17 1.386(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.3828(19) . ?
C17 H17 0.9500 . ?
C18 C19 1.3904(18) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 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
C9 N1 C10 112.87(10) . . ?
C9 N1 C14 121.59(10) . . ?
C10 N1 C14 125.43(10) . . ?
C12 N2 C7 113.03(9) . . ?
C12 N2 O3 106.42(8) . . ?
C7 N2 O3 102.44(8) . . ?
C2 O1 C20 116.84(10) . . ?
C1 O2 C21 111.57(9) . . ?
C11 O3 N2 100.92(8) . . ?
C6 C1 O2 120.12(10) . . ?
C6 C1 C2 120.15(11) . . ?
O2 C1 C2 119.70(10) . . ?
O1 C2 C3 125.18(11) . . ?
O1 C2 C1 116.10(11) . . ?
C3 C2 C1 118.72(11) . . ?
C2 C3 C4 121.09(11) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C5 C4 C3 119.53(11) . . ?
C5 C4 C13 120.17(11) . . ?
C3 C4 C13 120.28(11) . . ?
C4 C5 C6 119.19(11) . . ?
C4 C5 C7 122.11(10) . . ?
C6 C5 C7 118.64(10) . . ?
C1 C6 C5 121.30(11) . . ?
C1 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
N2 C7 C5 116.08(9) . . ?
N2 C7 C8 101.66(9) . . ?
C5 C7 C8 112.88(9) . . ?
N2 C7 H7 108.6 . . ?
C5 C7 H7 108.6 . . ?
C8 C7 H7 108.6 . . ?
C9 C8 C11 104.84(9) . . ?
C9 C8 C7 112.87(9) . . ?
C11 C8 C7 102.87(9) . . ?
C9 C8 H8 111.9 . . ?
C11 C8 H8 111.9 . . ?
C7 C8 H8 111.9 . . ?
O5 C9 N1 124.03(11) . . ?
O5 C9 C8 127.03(11) . . ?
N1 C9 C8 108.94(10) . . ?
O4 C10 N1 125.25(11) . . ?
O4 C10 C11 127.11(11) . . ?
N1 C10 C11 107.61(10) . . ?
O3 C11 C8 107.04(9) . . ?
O3 C11 C10 112.89(10) . . ?
C8 C11 C10 104.63(9) . . ?
O3 C11 H11 110.7 . . ?
C8 C11 H11 110.7 . . ?
C10 C11 H11 110.7 . . ?
N2 C12 C13 114.54(10) . . ?
N2 C12 H12A 108.6 . . ?
C13 C12 H12A 108.6 . . ?
N2 C12 H12B 108.6 . . ?
C13 C12 H12B 108.6 . . ?
H12A C12 H12B 107.6 . . ?
C4 C13 C12 111.61(10) . . ?
C4 C13 H13A 109.3 . . ?
C12 C13 H13A 109.3 . . ?
C4 C13 H13B 109.3 . . ?
C12 C13 H13B 109.3 . . ?
H13A C13 H13B 108.0 . . ?
C15 C14 C19 121.46(11) . . ?
C15 C14 N1 118.76(11) . . ?
C19 C14 N1 119.67(11) . . ?
C14 C15 C16 119.03(12) . . ?
C14 C15 H15 120.5 . . ?
C16 C15 H15 120.5 . . ?
C17 C16 C15 120.15(13) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C18 C17 C16 120.21(12) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C17 C18 C19 120.20(12) . . ?
C17 C18 H18 119.9 . . ?
C19 C18 H18 119.9 . . ?
C14 C19 C18 118.94(12) . . ?
C14 C19 H19 120.5 . . ?
C18 C19 H19 120.5 . . ?
O1 C20 H20A 109.5 . . ?
O1 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O1 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O2 C21 H21A 109.5 . . ?
O2 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
O2 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.55
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.307
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.060
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_oic242
_database_code_depnum_ccdc_archive 'CCDC 1006042'
_audit_update_record             
;
2014-05-30 deposited with the CCDC.
2016-11-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H18 N2 O5'
_chemical_formula_weight         318.32

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   P2(1)/c

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

_cell_length_a                   9.8243(10)
_cell_length_b                   8.6128(8)
_cell_length_c                   17.8328(18)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.843(5)
_cell_angle_gamma                90.00
_cell_volume                     1458.6(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2649
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      27.12

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.36
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.450
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             672
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9578
_exptl_absorpt_correction_T_max  0.9619
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13444
_diffrn_reflns_av_R_equivalents  0.0681
_diffrn_reflns_av_sigmaI/netI    0.0647
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.14
_diffrn_reflns_theta_max         27.57
_reflns_number_total             3284
_reflns_number_gt                2386
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0691P)²+0.0744P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3284
_refine_ls_number_parameters     211
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0731
_refine_ls_R_factor_gt           0.0499
_refine_ls_wR_factor_ref         0.1399
_refine_ls_wR_factor_gt          0.1267
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 1.06684(13) 0.44368(14) 0.68439(7) 0.0268(3) Uani 1 1 d . . .
O2 O 0.21901(12) 0.56678(13) 0.23510(7) 0.0238(3) Uani 1 1 d . . .
O3 O 0.31917(12) 0.29736(13) 0.27987(6) 0.0216(3) Uani 1 1 d . . .
O4 O 0.92732(12) 0.63808(13) 0.54603(6) 0.0207(3) Uani 1 1 d . . .
O5 O 0.72379(14) 0.17723(14) 0.51165(7) 0.0312(3) Uani 1 1 d . . .
N1 N 0.82523(14) 0.67051(16) 0.47304(8) 0.0202(3) Uani 1 1 d . . .
N2 N 0.90942(14) 0.27889(16) 0.60406(8) 0.0211(3) Uani 1 1 d . . .
C1 C 0.95941(17) 0.42236(19) 0.63403(10) 0.0206(4) Uani 1 1 d . . .
C2 C 0.85651(17) 0.54482(19) 0.59248(9) 0.0189(4) Uani 1 1 d . . .
H2 H 0.8197 0.6081 0.6286 0.023 Uiso 1 1 calc R . .
C3 C 0.74094(17) 0.45717(18) 0.53552(9) 0.0185(4) Uani 1 1 d . . .
H3 H 0.6486 0.4749 0.5454 0.022 Uiso 1 1 calc R . .
C4 C 0.74800(17) 0.52259(19) 0.45527(9) 0.0189(4) Uani 1 1 d . . .
H4 H 0.8050 0.4515 0.4330 0.023 Uiso 1 1 calc R . .
C5 C 0.60665(17) 0.54176(19) 0.39737(9) 0.0177(4) Uani 1 1 d . . .
C6 C 0.53183(17) 0.40795(19) 0.36621(9) 0.0182(4) Uani 1 1 d . . .
H6 H 0.5697 0.3106 0.3817 0.022 Uiso 1 1 calc R . .
C7 C 0.40256(17) 0.41899(19) 0.31272(9) 0.0183(4) Uani 1 1 d . . .
C8 C 0.34640(17) 0.56755(19) 0.28859(9) 0.0188(4) Uani 1 1 d . . .
C9 C 0.16177(18) 0.7146(2) 0.20619(10) 0.0258(4) Uani 1 1 d . . .
H9A H 0.1432 0.7744 0.2479 0.039 Uiso 1 1 calc R . .
H9B H 0.0757 0.6994 0.1668 0.039 Uiso 1 1 calc R . .
H9C H 0.2281 0.7689 0.1845 0.039 Uiso 1 1 calc R . .
C10 C 0.36502(18) 0.14529(18) 0.30651(10) 0.0218(4) Uani 1 1 d . . .
H10A H 0.4551 0.1251 0.2968 0.033 Uiso 1 1 calc R . .
H10B H 0.2980 0.0702 0.2794 0.033 Uiso 1 1 calc R . .
H10C H 0.3728 0.1381 0.3612 0.033 Uiso 1 1 calc R . .
C11 C 0.55060(18) 0.68826(19) 0.37518(10) 0.0191(4) Uani 1 1 d . . .
C12 C 0.62881(19) 0.83206(19) 0.40950(10) 0.0228(4) Uani 1 1 d . . .
H12A H 0.5623 0.9099 0.4172 0.027 Uiso 1 1 calc R . .
H12B H 0.6793 0.8740 0.3739 0.027 Uiso 1 1 calc R . .
C13 C 0.73216(18) 0.79561(19) 0.48652(10) 0.0222(4) Uani 1 1 d . . .
H13A H 0.7870 0.8871 0.5065 0.027 Uiso 1 1 calc R . .
H13B H 0.6820 0.7626 0.5241 0.027 Uiso 1 1 calc R . .
C14 C 0.78460(18) 0.28861(19) 0.54661(10) 0.0208(4) Uani 1 1 d . . .
C15 C 0.98400(19) 0.13408(19) 0.62709(11) 0.0265(4) Uani 1 1 d . . .
H15A H 1.0663 0.1534 0.6686 0.040 Uiso 1 1 calc R . .
H15B H 1.0116 0.0906 0.5837 0.040 Uiso 1 1 calc R . .
H15C H 0.9235 0.0625 0.6443 0.040 Uiso 1 1 calc R . .
C16 C 0.41972(17) 0.69887(19) 0.32054(10) 0.0199(4) Uani 1 1 d . . .
H16 H 0.3815 0.7963 0.3055 0.024 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.2118(19) . ?
O2 C8 1.3655(18) . ?
O2 C9 1.4330(19) . ?
O3 C7 1.3660(19) . ?
O3 C10 1.4263(18) . ?
O4 N1 1.4523(17) . ?
O4 C2 1.4528(19) . ?
O5 C14 1.214(2) . ?
N1 C13 1.472(2) . ?
N1 C4 1.475(2) . ?
N2 C14 1.384(2) . ?
N2 C1 1.385(2) . ?
N2 C15 1.451(2) . ?
C1 C2 1.516(2) . ?
C2 C3 1.517(2) . ?
C2 H2 0.9800 . ?
C3 C14 1.512(2) . ?
C3 C4 1.556(2) . ?
C3 H3 0.9800 . ?
C4 C5 1.512(2) . ?
C4 H4 0.9800 . ?
C5 C11 1.393(2) . ?
C5 C6 1.403(2) . ?
C6 C7 1.382(2) . ?
C6 H6 0.9300 . ?
C7 C8 1.416(2) . ?
C8 C16 1.383(2) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C16 1.403(2) . ?
C11 C12 1.503(2) . ?
C12 C13 1.517(2) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 O2 C9 116.87(13) . . ?
C7 O3 C10 117.25(13) . . ?
N1 O4 C2 107.21(11) . . ?
O4 N1 C13 108.04(12) . . ?
O4 N1 C4 103.04(11) . . ?
C13 N1 C4 111.12(13) . . ?
C14 N2 C1 113.00(14) . . ?
C14 N2 C15 123.27(14) . . ?
C1 N2 C15 123.63(14) . . ?
O1 C1 N2 125.20(15) . . ?
O1 C1 C2 126.99(15) . . ?
N2 C1 C2 107.81(13) . . ?
O4 C2 C1 107.85(13) . . ?
O4 C2 C3 106.20(12) . . ?
C1 C2 C3 105.79(13) . . ?
O4 C2 H2 112.2 . . ?
C1 C2 H2 112.2 . . ?
C3 C2 H2 112.2 . . ?
C14 C3 C2 104.58(13) . . ?
C14 C3 C4 112.95(14) . . ?
C2 C3 C4 103.52(13) . . ?
C14 C3 H3 111.8 . . ?
C2 C3 H3 111.8 . . ?
C4 C3 H3 111.8 . . ?
N1 C4 C5 112.59(13) . . ?
N1 C4 C3 104.88(12) . . ?
C5 C4 C3 114.71(13) . . ?
N1 C4 H4 108.1 . . ?
C5 C4 H4 108.1 . . ?
C3 C4 H4 108.1 . . ?
C11 C5 C6 120.18(15) . . ?
C11 C5 C4 121.33(14) . . ?
C6 C5 C4 118.49(14) . . ?
C7 C6 C5 120.81(15) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
O3 C7 C6 125.95(14) . . ?
O3 C7 C8 114.74(14) . . ?
C6 C7 C8 119.30(14) . . ?
O2 C8 C16 125.40(15) . . ?
O2 C8 C7 115.09(14) . . ?
C16 C8 C7 119.50(15) . . ?
O2 C9 H9A 109.5 . . ?
O2 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
O2 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O3 C10 H10A 109.5 . . ?
O3 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
O3 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C5 C11 C16 118.78(15) . . ?
C5 C11 C12 120.47(15) . . ?
C16 C11 C12 120.74(14) . . ?
C11 C12 C13 110.61(14) . . ?
C11 C12 H12A 109.5 . . ?
C13 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C13 C12 H12B 109.5 . . ?
H12A C12 H12B 108.1 . . ?
N1 C13 C12 107.66(14) . . ?
N1 C13 H13A 110.2 . . ?
C12 C13 H13A 110.2 . . ?
N1 C13 H13B 110.2 . . ?
C12 C13 H13B 110.2 . . ?
H13A C13 H13B 108.5 . . ?
O5 C14 N2 123.92(15) . . ?
O5 C14 C3 127.26(15) . . ?
N2 C14 C3 108.82(14) . . ?
N2 C15 H15A 109.5 . . ?
N2 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N2 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C8 C16 C11 121.38(15) . . ?
C8 C16 H16 119.3 . . ?
C11 C16 H16 119.3 . . ?

_diffrn_measured_fraction_theta_max 0.976
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.066
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_oicrf1_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1022997'
_audit_update_record             
;
2014-09-04 deposited with the CCDC.
2016-11-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H19 Br N O5.50'
_chemical_formula_weight         405.24

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables 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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

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

_cell_length_a                   11.0353(7)
_cell_length_b                   21.5973(13)
_cell_length_c                   15.0726(9)
_cell_angle_alpha                90
_cell_angle_beta                 101.886(3)
_cell_angle_gamma                90
_cell_volume                     3515.3(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9502
_cell_measurement_theta_min      3.63
_cell_measurement_theta_max      66.72

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.531
_exptl_crystal_F_000             1656
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    3.456
_shelx_estimated_absorpt_T_min   0.353
_shelx_estimated_absorpt_T_max   0.575
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.28
_exptl_absorpt_correction_T_max  0.59
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            46269
_diffrn_reflns_av_unetI/netI     0.0290
_diffrn_reflns_av_R_equivalents  0.0530
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.629
_diffrn_reflns_theta_max         66.827
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.978
_reflns_number_total             6216
_reflns_number_gt                5313
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0316P)²+3.5026P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6216
_refine_ls_number_parameters     444
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0443
_refine_ls_R_factor_gt           0.0351
_refine_ls_wR_factor_ref         0.0835
_refine_ls_wR_factor_gt          0.0794
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.002
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br -0.46885(3) 0.56278(2) 0.24302(2) 0.04146(10) Uani 1 1 d . . . . .
N1 N 0.36392(18) 0.64997(9) 0.51541(13) 0.0266(4) Uani 1 1 d . . . . .
O1 O 0.07510(15) 0.66998(7) 0.48154(12) 0.0289(4) Uani 1 1 d . . . . .
O2 O 0.29016(18) 0.73015(9) 0.41908(12) 0.0409(5) Uani 1 1 d . . . . .
O3 O -0.02059(17) 0.76259(8) 0.46049(15) 0.0437(5) Uani 1 1 d . . . . .
O4 O 0.12656(19) 0.56401(9) 0.65678(17) 0.0529(6) Uani 1 1 d . . . . .
O5 O 0.04126(18) 0.65713(9) 0.66222(15) 0.0465(5) Uani 1 1 d . . . . .
C1 C 0.3318(2) 0.61439(11) 0.58984(17) 0.0280(5) Uani 1 1 d . . . . .
H1 H 0.2956 0.5737 0.5665 0.034 Uiso 1 1 calc R U . . .
C2 C 0.4454(2) 0.60361(14) 0.66344(18) 0.0368(6) Uani 1 1 d . . . . .
H2A H 0.4249 0.5743 0.7087 0.044 Uiso 1 1 calc R U . . .
H2B H 0.4714 0.6432 0.6947 0.044 Uiso 1 1 calc R U . . .
C3 C 0.5523(3) 0.57739(14) 0.6244(2) 0.0394(6) Uani 1 1 d . . . . .
H3A H 0.6261 0.5718 0.6736 0.047 Uiso 1 1 calc R U . . .
H3B H 0.5288 0.5364 0.5966 0.047 Uiso 1 1 calc R U . . .
C4 C 0.5829(2) 0.62155(13) 0.55308(19) 0.0376(6) Uani 1 1 d . . . . .
H4A H 0.6113 0.6617 0.5818 0.045 Uiso 1 1 calc R U . . .
H4B H 0.6509 0.6040 0.5271 0.045 Uiso 1 1 calc R U . . .
C5 C 0.4706(2) 0.63186(14) 0.47841(18) 0.0362(6) Uani 1 1 d . . . . .
H5A H 0.4887 0.6647 0.4371 0.043 Uiso 1 1 calc R U . . .
H5B H 0.4512 0.5933 0.4428 0.043 Uiso 1 1 calc R U . . .
C6 C 0.2854(2) 0.69560(12) 0.48316(16) 0.0292(5) Uani 1 1 d . . . . .
C7 C 0.1842(2) 0.69736(11) 0.53740(16) 0.0267(5) Uani 1 1 d . . . . .
H7 H 0.1684 0.7403 0.5571 0.032 Uiso 1 1 calc R U . . .
C8 C 0.2312(2) 0.65460(11) 0.61777(17) 0.0283(5) Uani 1 1 d . . . . .
H8 H 0.2719 0.6810 0.6700 0.034 Uiso 1 1 calc R U . . .
C9 C 0.1298(2) 0.61880(13) 0.64692(18) 0.0351(6) Uani 1 1 d . . . . .
C10 C -0.0662(3) 0.62773(17) 0.6848(3) 0.0663(11) Uani 1 1 d . . . . .
H10A H -0.0990 0.5967 0.6385 0.099 Uiso 1 1 calc R U . . .
H10B H -0.1298 0.6590 0.6870 0.099 Uiso 1 1 calc R U . . .
H10C H -0.0427 0.6075 0.7440 0.099 Uiso 1 1 calc R U . . .
C11 C -0.0235(2) 0.70741(11) 0.45149(17) 0.0289(5) Uani 1 1 d . . . . .
C12 C -0.1326(2) 0.67114(11) 0.40620(16) 0.0261(5) Uani 1 1 d . . . . .
C13 C -0.2352(2) 0.70330(11) 0.35885(17) 0.0291(5) Uani 1 1 d . . . . .
H13 H -0.2354 0.7473 0.3592 0.035 Uiso 1 1 calc R U . . .
C14 C -0.3367(2) 0.67145(12) 0.31130(17) 0.0302(6) Uani 1 1 d . . . . .
H14 H -0.4062 0.6931 0.2778 0.036 Uiso 1 1 calc R U . . .
C15 C -0.3351(2) 0.60758(12) 0.31343(17) 0.0286(5) Uani 1 1 d . . . . .
C16 C -0.2366(2) 0.57463(12) 0.36245(18) 0.0308(6) Uani 1 1 d . . . . .
H16 H -0.2390 0.5307 0.3645 0.037 Uiso 1 1 calc R U . . .
C17 C -0.1345(2) 0.60680(11) 0.40852(17) 0.0280(5) Uani 1 1 d . . . . .
H17 H -0.0653 0.5848 0.4419 0.034 Uiso 1 1 calc R U . . .
Br1A Br 1.20650(3) 0.55066(2) 0.32483(2) 0.04927(11) Uani 1 1 d . . . . .
N1A N 0.37578(18) 0.63602(9) 0.03817(13) 0.0258(4) Uani 1 1 d . . . . .
O1A O 0.66442(15) 0.65391(7) 0.07404(11) 0.0252(3) Uani 1 1 d . . . . .
O2A O 0.44731(17) 0.72024(8) 0.12659(12) 0.0342(4) Uani 1 1 d . . . . .
O3A O 0.76414(17) 0.74577(8) 0.08665(14) 0.0402(5) Uani 1 1 d . . . . .
O4A O 0.61329(16) 0.53977(8) -0.08900(13) 0.0362(4) Uani 1 1 d . . . . .
O5A O 0.70394(17) 0.63105(8) -0.10346(12) 0.0359(4) Uani 1 1 d . . . . .
C1A C 0.4069(2) 0.59727(10) -0.03385(16) 0.0237(5) Uani 1 1 d . . . . .
H1A H 0.4400 0.5565 -0.0084 0.028 Uiso 1 1 calc R U . . .
C2A C 0.2920(2) 0.58739(12) -0.10775(17) 0.0318(6) Uani 1 1 d . . . . .
H2A1 H 0.2690 0.6268 -0.1404 0.038 Uiso 1 1 calc R U . . .
H2A2 H 0.3102 0.5567 -0.1520 0.038 Uiso 1 1 calc R U . . .
C3A C 0.1837(2) 0.56459(13) -0.06799(19) 0.0366(6) Uani 1 1 d . . . . .
H3A1 H 0.2040 0.5236 -0.0394 0.044 Uiso 1 1 calc R U . . .
H3A2 H 0.1094 0.5599 -0.1171 0.044 Uiso 1 1 calc R U . . .
C4A C 0.1561(2) 0.61020(13) 0.0026(2) 0.0382(6) Uani 1 1 d . . . . .
H4A1 H 0.1303 0.6504 -0.0268 0.046 Uiso 1 1 calc R U . . .
H4A2 H 0.0871 0.5942 0.0289 0.046 Uiso 1 1 calc R U . . .
C5A C 0.2701(2) 0.61946(13) 0.07744(18) 0.0351(6) Uani 1 1 d . . . . .
H5A1 H 0.2543 0.6527 0.1188 0.042 Uiso 1 1 calc R U . . .
H5A2 H 0.2883 0.5808 0.1131 0.042 Uiso 1 1 calc R U . . .
C6A C 0.4534(2) 0.68247(11) 0.06646(16) 0.0268(5) Uani 1 1 d . . . . .
C7A C 0.5569(2) 0.68026(11) 0.01389(16) 0.0252(5) Uani 1 1 d . . . . .
H7A H 0.5748 0.7220 -0.0090 0.030 Uiso 1 1 calc R U . . .
C8A C 0.5105(2) 0.63475(11) -0.06356(15) 0.0247(5) Uani 1 1 d . . . . .
H8A H 0.4728 0.6591 -0.1187 0.030 Uiso 1 1 calc R U . . .
C9A C 0.6122(2) 0.59521(12) -0.08617(15) 0.0265(5) Uani 1 1 d . . . . .
C10A C 0.8137(3) 0.59846(15) -0.1144(2) 0.0439(7) Uani 1 1 d . . . . .
H10D H 0.8449 0.5734 -0.0603 0.066 Uiso 1 1 calc R U . . .
H10E H 0.8772 0.6284 -0.1228 0.066 Uiso 1 1 calc R U . . .
H10F H 0.7938 0.5714 -0.1677 0.066 Uiso 1 1 calc R U . . .
C11A C 0.7631(2) 0.69107(11) 0.10182(16) 0.0264(5) Uani 1 1 d . . . . .
C12A C 0.8705(2) 0.65526(11) 0.15380(15) 0.0245(5) Uani 1 1 d . . . . .
C13A C 0.9788(2) 0.68745(12) 0.18990(17) 0.0304(6) Uani 1 1 d . . . . .
H13A H 0.9835 0.7307 0.1795 0.036 Uiso 1 1 calc R U . . .
C14A C 1.0794(2) 0.65676(13) 0.24073(18) 0.0336(6) Uani 1 1 d . . . . .
H14A H 1.1534 0.6785 0.2658 0.040 Uiso 1 1 calc R U . . .
C15A C 1.0700(2) 0.59387(12) 0.25429(17) 0.0307(6) Uani 1 1 d . . . . .
C16A C 0.9640(2) 0.56078(12) 0.21882(18) 0.0320(6) Uani 1 1 d . . . . .
H16A H 0.9600 0.5175 0.2289 0.038 Uiso 1 1 calc R U . . .
C17A C 0.8640(2) 0.59205(11) 0.16829(16) 0.0276(5) Uani 1 1 d . . . . .
H17A H 0.7902 0.5701 0.1433 0.033 Uiso 1 1 calc R U . . .
O1W O 0.3902(2) 0.76575(10) 0.28108(14) 0.0547(6) Uani 1 1 d . . . . .
H1WA H 0.4040 0.7352 0.2317 0.066 Uiso 1 1 d R U . . .
H2WA H 0.3469 0.7400 0.3227 0.066 Uiso 1 1 d R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C15 1.897(3) . ?
N1 C6 1.336(3) . ?
N1 C5 1.456(3) . ?
N1 C1 1.462(3) . ?
O1 C11 1.356(3) . ?
O1 C7 1.446(3) . ?
O2 C6 1.230(3) . ?
O3 C11 1.199(3) . ?
O4 C9 1.194(3) . ?
O5 C9 1.336(3) . ?
O5 C10 1.446(4) . ?
C1 C2 1.511(4) . ?
C1 C8 1.535(3) . ?
C1 H1 1.0000 . ?
C2 C3 1.532(4) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.526(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.509(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.514(3) . ?
C7 C8 1.527(3) . ?
C7 H7 1.0000 . ?
C8 C9 1.499(4) . ?
C8 H8 1.0000 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.480(3) . ?
C12 C17 1.390(3) . ?
C12 C13 1.393(3) . ?
C13 C14 1.382(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.380(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.379(4) . ?
C16 C17 1.383(4) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
Br1A C15A 1.900(3) . ?
N1A C6A 1.331(3) . ?
N1A C5A 1.457(3) . ?
N1A C1A 1.467(3) . ?
O1A C11A 1.348(3) . ?
O1A C7A 1.452(3) . ?
O2A C6A 1.231(3) . ?
O3A C11A 1.204(3) . ?
O4A C9A 1.198(3) . ?
O5A C9A 1.342(3) . ?
O5A C10A 1.440(3) . ?
C1A C2A 1.521(3) . ?
C1A C8A 1.540(3) . ?
C1A H1A 1.0000 . ?
C2A C3A 1.524(4) . ?
C2A H2A1 0.9900 . ?
C2A H2A2 0.9900 . ?
C3A C4A 1.526(4) . ?
C3A H3A1 0.9900 . ?
C3A H3A2 0.9900 . ?
C4A C5A 1.520(4) . ?
C4A H4A1 0.9900 . ?
C4A H4A2 0.9900 . ?
C5A H5A1 0.9900 . ?
C5A H5A2 0.9900 . ?
C6A C7A 1.519(4) . ?
C7A C8A 1.531(3) . ?
C7A H7A 1.0000 . ?
C8A C9A 1.504(3) . ?
C8A H8A 1.0000 . ?
C10A H10D 0.9800 . ?
C10A H10E 0.9800 . ?
C10A H10F 0.9800 . ?
C11A C12A 1.495(3) . ?
C12A C17A 1.387(3) . ?
C12A C13A 1.393(3) . ?
C13A C14A 1.381(4) . ?
C13A H13A 0.9500 . ?
C14A C15A 1.381(4) . ?
C14A H14A 0.9500 . ?
C15A C16A 1.381(4) . ?
C16A C17A 1.382(3) . ?
C16A H16A 0.9500 . ?
C17A H17A 0.9500 . ?
O1W H1WA 1.0290 . ?
O1W H2WA 1.0268 . ?

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 N1 C5 125.0(2) . . ?
C6 N1 C1 115.2(2) . . ?
C5 N1 C1 119.7(2) . . ?
C11 O1 C7 117.73(18) . . ?
C9 O5 C10 115.6(2) . . ?
N1 C1 C2 110.4(2) . . ?
N1 C1 C8 102.48(19) . . ?
C2 C1 C8 115.0(2) . . ?
N1 C1 H1 109.5 . . ?
C2 C1 H1 109.5 . . ?
C8 C1 H1 109.5 . . ?
C1 C2 C3 111.3(2) . . ?
C1 C2 H2A 109.4 . . ?
C3 C2 H2A 109.4 . . ?
C1 C2 H2B 109.4 . . ?
C3 C2 H2B 109.4 . . ?
H2A C2 H2B 108.0 . . ?
C4 C3 C2 109.8(2) . . ?
C4 C3 H3A 109.7 . . ?
C2 C3 H3A 109.7 . . ?
C4 C3 H3B 109.7 . . ?
C2 C3 H3B 109.7 . . ?
H3A C3 H3B 108.2 . . ?
C5 C4 C3 110.5(2) . . ?
C5 C4 H4A 109.5 . . ?
C3 C4 H4A 109.5 . . ?
C5 C4 H4B 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 108.1 . . ?
N1 C5 C4 111.0(2) . . ?
N1 C5 H5A 109.4 . . ?
C4 C5 H5A 109.4 . . ?
N1 C5 H5B 109.4 . . ?
C4 C5 H5B 109.4 . . ?
H5A C5 H5B 108.0 . . ?
O2 C6 N1 127.1(2) . . ?
O2 C6 C7 124.4(2) . . ?
N1 C6 C7 108.5(2) . . ?
O1 C7 C6 107.07(19) . . ?
O1 C7 C8 108.69(19) . . ?
C6 C7 C8 104.24(19) . . ?
O1 C7 H7 112.1 . . ?
C6 C7 H7 112.1 . . ?
C8 C7 H7 112.1 . . ?
C9 C8 C7 113.1(2) . . ?
C9 C8 C1 114.5(2) . . ?
C7 C8 C1 105.73(19) . . ?
C9 C8 H8 107.7 . . ?
C7 C8 H8 107.7 . . ?
C1 C8 H8 107.7 . . ?
O4 C9 O5 123.4(3) . . ?
O4 C9 C8 126.2(2) . . ?
O5 C9 C8 110.3(2) . . ?
O5 C10 H10A 109.5 . . ?
O5 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
O5 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O3 C11 O1 123.6(2) . . ?
O3 C11 C12 125.3(2) . . ?
O1 C11 C12 111.0(2) . . ?
C17 C12 C13 119.8(2) . . ?
C17 C12 C11 122.2(2) . . ?
C13 C12 C11 118.1(2) . . ?
C14 C13 C12 120.2(2) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C13 C14 C15 118.7(2) . . ?
C13 C14 H14 120.6 . . ?
C15 C14 H14 120.6 . . ?
C16 C15 C14 122.2(2) . . ?
C16 C15 Br1 118.22(19) . . ?
C14 C15 Br1 119.49(19) . . ?
C15 C16 C17 118.7(2) . . ?
C15 C16 H16 120.6 . . ?
C17 C16 H16 120.6 . . ?
C16 C17 C12 120.3(2) . . ?
C16 C17 H17 119.9 . . ?
C12 C17 H17 119.9 . . ?
C6A N1A C5A 124.8(2) . . ?
C6A N1A C1A 115.69(19) . . ?
C5A N1A C1A 119.33(19) . . ?
C11A O1A C7A 117.66(18) . . ?
C9A O5A C10A 115.3(2) . . ?
N1A C1A C2A 109.55(19) . . ?
N1A C1A C8A 102.50(18) . . ?
C2A C1A C8A 114.7(2) . . ?
N1A C1A H1A 109.9 . . ?
C2A C1A H1A 109.9 . . ?
C8A C1A H1A 109.9 . . ?
C3A C2A C1A 111.1(2) . . ?
C3A C2A H2A1 109.4 . . ?
C1A C2A H2A1 109.4 . . ?
C3A C2A H2A2 109.4 . . ?
C1A C2A H2A2 109.4 . . ?
H2A1 C2A H2A2 108.0 . . ?
C2A C3A C4A 110.5(2) . . ?
C2A C3A H3A1 109.5 . . ?
C4A C3A H3A1 109.5 . . ?
C2A C3A H3A2 109.5 . . ?
C4A C3A H3A2 109.5 . . ?
H3A1 C3A H3A2 108.1 . . ?
C5A C4A C3A 110.4(2) . . ?
C5A C4A H4A1 109.6 . . ?
C3A C4A H4A1 109.6 . . ?
C5A C4A H4A2 109.6 . . ?
C3A C4A H4A2 109.6 . . ?
H4A1 C4A H4A2 108.1 . . ?
N1A C5A C4A 109.9(2) . . ?
N1A C5A H5A1 109.7 . . ?
C4A C5A H5A1 109.7 . . ?
N1A C5A H5A2 109.7 . . ?
C4A C5A H5A2 109.7 . . ?
H5A1 C5A H5A2 108.2 . . ?
O2A C6A N1A 127.3(2) . . ?
O2A C6A C7A 124.5(2) . . ?
N1A C6A C7A 108.23(19) . . ?
O1A C7A C6A 106.97(18) . . ?
O1A C7A C8A 109.05(18) . . ?
C6A C7A C8A 104.38(19) . . ?
O1A C7A H7A 112.0 . . ?
C6A C7A H7A 112.0 . . ?
C8A C7A H7A 112.0 . . ?
C9A C8A C7A 112.9(2) . . ?
C9A C8A C1A 113.60(19) . . ?
C7A C8A C1A 105.52(19) . . ?
C9A C8A H8A 108.2 . . ?
C7A C8A H8A 108.2 . . ?
C1A C8A H8A 108.2 . . ?
O4A C9A O5A 123.8(2) . . ?
O4A C9A C8A 126.1(2) . . ?
O5A C9A C8A 110.2(2) . . ?
O5A C10A H10D 109.5 . . ?
O5A C10A H10E 109.5 . . ?
H10D C10A H10E 109.5 . . ?
O5A C10A H10F 109.5 . . ?
H10D C10A H10F 109.5 . . ?
H10E C10A H10F 109.5 . . ?
O3A C11A O1A 124.3(2) . . ?
O3A C11A C12A 124.7(2) . . ?
O1A C11A C12A 110.9(2) . . ?
C17A C12A C13A 119.9(2) . . ?
C17A C12A C11A 122.0(2) . . ?
C13A C12A C11A 118.1(2) . . ?
C14A C13A C12A 120.3(2) . . ?
C14A C13A H13A 119.9 . . ?
C12A C13A H13A 119.9 . . ?
C15A C14A C13A 118.6(2) . . ?
C15A C14A H14A 120.7 . . ?
C13A C14A H14A 120.7 . . ?
C16A C15A C14A 122.3(2) . . ?
C16A C15A Br1A 118.2(2) . . ?
C14A C15A Br1A 119.42(19) . . ?
C15A C16A C17A 118.5(2) . . ?
C15A C16A H16A 120.7 . . ?
C17A C16A H16A 120.7 . . ?
C16A C17A C12A 120.4(2) . . ?
C16A C17A H17A 119.8 . . ?
C12A C17A H17A 119.8 . . ?
H1WA O1W H2WA 104.6 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1W H2WA O2 1.03 1.71 2.661(3) 152.2 .
O1W H1WA O2A 1.03 1.78 2.718(3) 150.3 .
C8A H8A O1W 1.00 2.27 3.253(3) 165.7 4_575
C5A H5A2 Br1 0.99 3.00 3.615(3) 121.2 1_655
C4A H4A1 O3 0.99 2.49 3.353(3) 145.3 4_575
C16 H16 O4 0.95 2.45 3.266(3) 144.4 3_566
C14 H14 O2A 0.95 2.58 3.437(3) 150.8 1_455
C8 H8 O1W 1.00 2.22 3.212(3) 171.0 4_576
C5 H5B Br1A 0.99 3.05 3.761(3) 129.5 1_455
C4 H4A O3A 0.99 2.61 3.471(3) 145.9 4_576
C2 H2B O1W 0.99 2.62 3.453(3) 142.3 4_576
C2 H2A Br1 0.99 3.06 3.849(3) 137.2 3_566

_refine_diff_density_max         0.356
_refine_diff_density_min         -0.614
_refine_diff_density_rms         0.059

_shelxl_version_number           2014-3

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

data_oic248rb
_database_code_depnum_ccdc_archive 'CCDC 1051097'
_audit_update_record             
;
2015-02-24 deposited with the CCDC.
2016-11-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H12 N2 O3'
_chemical_formula_sum            'C9 H12 N2 O3'
_chemical_formula_weight         196.21

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

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pna2(1)
_symmetry_space_group_name_Hall  'P 2c -2n'
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'

_cell_length_a                   7.9208(3)
_cell_length_b                   16.5681(9)
_cell_length_c                   6.7713(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     888.62(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2445
_cell_measurement_theta_min      2.46
_cell_measurement_theta_max      27.58

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.467
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             416
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9620
_exptl_absorpt_correction_T_max  0.9889
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4579
_diffrn_reflns_av_R_equivalents  0.0210
_diffrn_reflns_av_sigmaI/netI    0.0280
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.46
_diffrn_reflns_theta_max         27.63
_reflns_number_total             2018
_reflns_number_gt                1913
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0440P)²+0.0000P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   ?
_refine_ls_number_reflns         2018
_refine_ls_number_parameters     128
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0363
_refine_ls_R_factor_gt           0.0338
_refine_ls_wR_factor_ref         0.0873
_refine_ls_wR_factor_gt          0.0847
_refine_ls_goodness_of_fit_ref   1.279
_refine_ls_restrained_S_all      1.279
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.87160(12) 0.65515(7) 0.66420(18) 0.0158(2) Uani 1 1 d . . .
O2 O 0.60741(13) 0.68810(7) 0.97928(18) 0.0193(3) Uani 1 1 d . . .
O3 O 0.37857(13) 0.53697(7) 0.4852(2) 0.0216(3) Uani 1 1 d . . .
N1 N 0.78684(15) 0.67915(8) 0.4753(2) 0.0137(3) Uani 1 1 d . . .
N2 N 0.45790(15) 0.62008(8) 0.7399(2) 0.0135(3) Uani 1 1 d . . .
C1 C 1.0152(2) 0.64162(10) 0.2496(3) 0.0220(4) Uani 1 1 d . . .
H1A H 1.0128 0.6476 0.1042 0.026 Uiso 1 1 calc R . .
H1B H 1.1343 0.6390 0.2937 0.026 Uiso 1 1 calc R . .
C2 C 0.91860(18) 0.56548(10) 0.3138(3) 0.0182(3) Uani 1 1 d . . .
H2A H 0.9003 0.5288 0.2004 0.022 Uiso 1 1 calc R . .
H2B H 0.9807 0.5361 0.4183 0.022 Uiso 1 1 calc R . .
C3 C 0.74994(18) 0.59818(9) 0.3924(2) 0.0137(3) Uani 1 1 d . . .
H3 H 0.6648 0.6020 0.2837 0.016 Uiso 1 1 calc R . .
C4 C 0.67690(17) 0.55294(9) 0.5699(3) 0.0140(3) Uani 1 1 d . . .
H4 H 0.7081 0.4945 0.5706 0.017 Uiso 1 1 calc R . .
C5 C 0.48756(18) 0.56635(9) 0.5879(2) 0.0138(3) Uani 1 1 d . . .
C6 C 0.29016(18) 0.65096(10) 0.7871(3) 0.0180(3) Uani 1 1 d . . .
H6A H 0.2130 0.6056 0.8094 0.022 Uiso 1 1 calc R . .
H6B H 0.2487 0.6838 0.6769 0.022 Uiso 1 1 calc R . .
H6C H 0.2962 0.6842 0.9066 0.022 Uiso 1 1 calc R . .
C7 C 0.60359(18) 0.64255(9) 0.8401(2) 0.0142(3) Uani 1 1 d . . .
C8 C 0.75403(18) 0.59961(9) 0.7443(2) 0.0139(3) Uani 1 1 d . . .
H8 H 0.8100 0.5621 0.8398 0.017 Uiso 1 1 calc R . .
C9 C 0.92245(18) 0.71245(10) 0.3501(3) 0.0183(3) Uani 1 1 d . . .
H9A H 1.0025 0.7439 0.4317 0.022 Uiso 1 1 calc R . .
H9B H 0.8739 0.7488 0.2488 0.022 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C8 1.4173(18) . ?
O1 N1 1.4984(17) . ?
O2 C7 1.208(2) . ?
O3 C5 1.2107(19) . ?
N1 C9 1.4756(19) . ?
N1 C3 1.4834(19) . ?
N2 C5 1.381(2) . ?
N2 C7 1.3895(19) . ?
N2 C6 1.4591(18) . ?
C1 C2 1.538(2) . ?
C1 C9 1.543(2) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.537(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.530(2) . ?
C3 H3 1.0000 . ?
C4 C5 1.5210(19) . ?
C4 C8 1.539(2) . ?
C4 H4 1.0000 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C8 1.532(2) . ?
C8 H8 1.0000 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?

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
C8 O1 N1 101.81(10) . . ?
C9 N1 C3 105.31(12) . . ?
C9 N1 O1 105.28(10) . . ?
C3 N1 O1 99.87(11) . . ?
C5 N2 C7 113.29(12) . . ?
C5 N2 C6 122.96(13) . . ?
C7 N2 C6 123.74(14) . . ?
C2 C1 C9 105.22(12) . . ?
C2 C1 H1A 110.7 . . ?
C9 C1 H1A 110.7 . . ?
C2 C1 H1B 110.7 . . ?
C9 C1 H1B 110.7 . . ?
H1A C1 H1B 108.8 . . ?
C3 C2 C1 103.95(13) . . ?
C3 C2 H2A 111.0 . . ?
C1 C2 H2A 111.0 . . ?
C3 C2 H2B 111.0 . . ?
C1 C2 H2B 111.0 . . ?
H2A C2 H2B 109.0 . . ?
N1 C3 C4 102.73(12) . . ?
N1 C3 C2 106.19(12) . . ?
C4 C3 C2 115.35(13) . . ?
N1 C3 H3 110.7 . . ?
C4 C3 H3 110.7 . . ?
C2 C3 H3 110.7 . . ?
C5 C4 C3 111.37(12) . . ?
C5 C4 C8 104.86(12) . . ?
C3 C4 C8 101.94(11) . . ?
C5 C4 H4 112.6 . . ?
C3 C4 H4 112.6 . . ?
C8 C4 H4 112.6 . . ?
O3 C5 N2 124.46(14) . . ?
O3 C5 C4 126.74(15) . . ?
N2 C5 C4 108.77(13) . . ?
N2 C6 H6A 109.5 . . ?
N2 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
N2 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
O2 C7 N2 124.70(14) . . ?
O2 C7 C8 126.94(14) . . ?
N2 C7 C8 108.36(13) . . ?
O1 C8 C7 111.82(12) . . ?
O1 C8 C4 107.05(12) . . ?
C7 C8 C4 104.45(11) . . ?
O1 C8 H8 111.1 . . ?
C7 C8 H8 111.1 . . ?
C4 C8 H8 111.1 . . ?
N1 C9 C1 108.40(13) . . ?
N1 C9 H9A 110.0 . . ?
C1 C9 H9A 110.0 . . ?
N1 C9 H9B 110.0 . . ?
C1 C9 H9B 110.0 . . ?
H9A C9 H9B 108.4 . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        27.63
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.043
