# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/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_bo2950
_database_code_depnum_ccdc_archive 'CCDC 1055698'
_audit_update_record             
;
2015-03-24 deposited with the CCDC.
2015-08-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H13 N O3'
_chemical_formula_weight         279.28

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)

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                   11.482(3)
_cell_length_b                   6.0114(13)
_cell_length_c                   19.382(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1337.8(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    4767
_cell_measurement_theta_min      2.062
_cell_measurement_theta_max      29.114

_exptl_crystal_description       Prism
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             584
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      153(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  AFC10/Saturn724+
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            11057
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_av_sigmaI/netI    0.0333
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         3.55
_diffrn_reflns_theta_max         29.11
_reflns_number_total             3340
_reflns_number_gt                3175
_reflns_threshold_expression     >2sigma(I)

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

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0469P)²+0.1560P] 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     SHELXL
_refine_ls_extinction_coef       0.005(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.4(8)
_refine_ls_number_reflns         3340
_refine_ls_number_parameters     192
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0403
_refine_ls_R_factor_gt           0.0375
_refine_ls_wR_factor_ref         0.0891
_refine_ls_wR_factor_gt          0.0868
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_restrained_S_all      1.002
_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 0.59713(10) -0.02884(17) 0.27235(6) 0.0305(3) Uani 1 1 d . . .
O2 O 0.66214(9) 0.21394(19) 0.35058(6) 0.0327(3) Uani 1 1 d . . .
N1 N 0.49941(12) -0.0532(2) 0.22629(7) 0.0293(3) Uani 1 1 d . . .
O3 O 0.48498(10) 1.14427(18) 0.49963(6) 0.0328(3) Uani 1 1 d . . .
C1 C 0.47472(12) 0.9643(2) 0.45807(7) 0.0244(3) Uani 1 1 d . . .
C2 C 0.37087(13) 0.9503(3) 0.42080(8) 0.0267(3) Uani 1 1 d . . .
H2 H 0.3123 1.0602 0.4266 0.032 Uiso 1 1 calc R . .
C3 C 0.35360(12) 0.7762(3) 0.37551(8) 0.0250(3) Uani 1 1 d . . .
H3 H 0.2823 0.7667 0.3508 0.030 Uiso 1 1 calc R . .
C4 C 0.43984(12) 0.6117(2) 0.36516(8) 0.0221(3) Uani 1 1 d . . .
C5 C 0.54219(13) 0.6270(2) 0.40461(8) 0.0256(3) Uani 1 1 d . . .
H5 H 0.6006 0.5162 0.3997 0.031 Uiso 1 1 calc R . .
C6 C 0.55969(13) 0.7997(3) 0.45034(8) 0.0265(3) Uani 1 1 d . . .
H6 H 0.6295 0.8067 0.4766 0.032 Uiso 1 1 calc R . .
C7 C 0.41618(12) 0.4480(2) 0.31293(8) 0.0223(3) Uani 1 1 d . . .
H7 H 0.3431 0.4686 0.2908 0.027 Uiso 1 1 calc R . .
C8 C 0.58667(13) 0.1652(2) 0.30948(8) 0.0255(3) Uani 1 1 d . . .
C9 C 0.47680(12) 0.2684(2) 0.28834(7) 0.0223(3) Uani 1 1 d . . .
C10 C 0.43273(13) 0.1181(2) 0.23604(8) 0.0237(3) Uani 1 1 d . . .
C11 C 0.32617(12) 0.1401(2) 0.19392(8) 0.0232(3) Uani 1 1 d . . .
C12 C 0.24712(13) -0.0344(2) 0.18972(8) 0.0280(3) Uani 1 1 d . . .
H12 H 0.2592 -0.1650 0.2163 0.034 Uiso 1 1 calc R . .
C13 C 0.15046(15) -0.0189(3) 0.14680(9) 0.0320(3) Uani 1 1 d . . .
H13 H 0.0961 -0.1378 0.1445 0.038 Uiso 1 1 calc R . .
C14 C 0.13377(14) 0.1710(3) 0.10732(9) 0.0337(4) Uani 1 1 d . . .
H14 H 0.0691 0.1800 0.0769 0.040 Uiso 1 1 calc R . .
C15 C 0.21092(13) 0.3476(3) 0.11203(9) 0.0315(3) Uani 1 1 d . . .
H15 H 0.1984 0.4781 0.0854 0.038 Uiso 1 1 calc R . .
C16 C 0.30676(13) 0.3336(2) 0.15574(8) 0.0269(3) Uani 1 1 d . . .
H16 H 0.3590 0.4556 0.1596 0.032 Uiso 1 1 calc R . .
C17 C 0.59465(16) 1.1791(3) 0.53300(10) 0.0391(4) Uani 1 1 d . . .
H17A H 0.6098 1.0564 0.5651 0.047 Uiso 1 1 calc R . .
H17B H 0.5926 1.3197 0.5585 0.047 Uiso 1 1 calc R . .
H17C H 0.6566 1.1848 0.4983 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
O1 C8 1.3757(19) . ?
O1 N1 1.4413(18) . ?
O2 C8 1.2130(19) . ?
N1 C10 1.2971(19) . ?
O3 C1 1.3542(18) . ?
O3 C17 1.431(2) . ?
C1 C2 1.397(2) . ?
C1 C6 1.398(2) . ?
C2 C3 1.380(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.414(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.405(2) . ?
C4 C7 1.438(2) . ?
C5 C6 1.380(2) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C9 1.370(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.465(2) . ?
C9 C10 1.449(2) . ?
C10 C11 1.477(2) . ?
C11 C12 1.390(2) . ?
C11 C16 1.397(2) . ?
C12 C13 1.390(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.388(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.386(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.391(2) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 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
C8 O1 N1 110.02(10) . . ?
C10 N1 O1 106.78(12) . . ?
C1 O3 C17 117.53(13) . . ?
O3 C1 C2 115.47(13) . . ?
O3 C1 C6 124.66(13) . . ?
C2 C1 C6 119.86(14) . . ?
C3 C2 C1 119.82(14) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C2 C3 C4 121.33(14) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C5 C4 C3 117.57(13) . . ?
C5 C4 C7 125.87(13) . . ?
C3 C4 C7 116.52(13) . . ?
C6 C5 C4 121.38(14) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C5 C6 C1 119.98(14) . . ?
C5 C6 H6 120.0 . . ?
C1 C6 H6 120.0 . . ?
C9 C7 C4 133.50(13) . . ?
C9 C7 H7 113.3 . . ?
C4 C7 H7 113.3 . . ?
O2 C8 O1 119.09(13) . . ?
O2 C8 C9 134.15(15) . . ?
O1 C8 C9 106.75(13) . . ?
C7 C9 C10 123.86(13) . . ?
C7 C9 C8 132.41(14) . . ?
C10 C9 C8 103.42(12) . . ?
N1 C10 C9 113.01(14) . . ?
N1 C10 C11 118.66(14) . . ?
C9 C10 C11 128.32(13) . . ?
C12 C11 C16 119.57(14) . . ?
C12 C11 C10 120.40(13) . . ?
C16 C11 C10 119.98(13) . . ?
C11 C12 C13 120.41(14) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
C14 C13 C12 119.69(15) . . ?
C14 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
C15 C14 C13 120.37(15) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C14 C15 C16 119.98(15) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C15 C16 C11 119.94(14) . . ?
C15 C16 H16 120.0 . . ?
C11 C16 H16 120.0 . . ?
O3 C17 H17A 109.5 . . ?
O3 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O3 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 O1 N1 C10 -0.62(16) . . . . ?
C17 O3 C1 C2 -173.28(15) . . . . ?
C17 O3 C1 C6 6.1(2) . . . . ?
O3 C1 C2 C3 178.14(13) . . . . ?
C6 C1 C2 C3 -1.3(2) . . . . ?
C1 C2 C3 C4 -0.8(2) . . . . ?
C2 C3 C4 C5 2.4(2) . . . . ?
C2 C3 C4 C7 -175.35(14) . . . . ?
C3 C4 C5 C6 -1.9(2) . . . . ?
C7 C4 C5 C6 175.58(14) . . . . ?
C4 C5 C6 C1 -0.1(2) . . . . ?
O3 C1 C6 C5 -177.62(14) . . . . ?
C2 C1 C6 C5 1.7(2) . . . . ?
C5 C4 C7 C9 2.2(3) . . . . ?
C3 C4 C7 C9 179.65(15) . . . . ?
N1 O1 C8 O2 -179.35(13) . . . . ?
N1 O1 C8 C9 1.51(14) . . . . ?
C4 C7 C9 C10 177.42(15) . . . . ?
C4 C7 C9 C8 4.9(3) . . . . ?
O2 C8 C9 C7 -7.1(3) . . . . ?
O1 C8 C9 C7 171.86(15) . . . . ?
O2 C8 C9 C10 179.30(17) . . . . ?
O1 C8 C9 C10 -1.75(14) . . . . ?
O1 N1 C10 C9 -0.59(17) . . . . ?
O1 N1 C10 C11 178.46(12) . . . . ?
C7 C9 C10 N1 -172.85(14) . . . . ?
C8 C9 C10 N1 1.47(17) . . . . ?
C7 C9 C10 C11 8.2(2) . . . . ?
C8 C9 C10 C11 -177.46(14) . . . . ?
N1 C10 C11 C12 52.1(2) . . . . ?
C9 C10 C11 C12 -129.02(16) . . . . ?
N1 C10 C11 C16 -125.25(16) . . . . ?
C9 C10 C11 C16 53.6(2) . . . . ?
C16 C11 C12 C13 1.3(2) . . . . ?
C10 C11 C12 C13 -176.07(15) . . . . ?
C11 C12 C13 C14 0.8(2) . . . . ?
C12 C13 C14 C15 -1.9(3) . . . . ?
C13 C14 C15 C16 1.0(3) . . . . ?
C14 C15 C16 C11 1.1(2) . . . . ?
C12 C11 C16 C15 -2.2(2) . . . . ?
C10 C11 C16 C15 175.14(14) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        29.11
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.153
_refine_diff_density_min         -0.144
_refine_diff_density_rms         0.033
