# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_ho89b
_database_code_depnum_ccdc_archive 'CCDC 1519664'
_audit_update_record             
;
2016-11-28 deposited with the CCDC.
2017-03-13 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT183_ho89b               
;
PROBLEM: Missing _cell_measurement_reflns_used value ....     Please Do !
RESPONSE: The cell parameters were refined after the measurement of all data
;
# Added during the CSD deposition process: Monday 28 November 2016 02:51 PM
# end Validation Reply Form



_diffrn_measurement_device_type  'BRUKER APEX'
#Added by publCIF


_publcif_datablock.id            {567a0a2b-0ba4-4873-83f9-9e96daa35e27}

_audit_creation_date             2016-05-18T11:52:29-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H10 N2 O2'
_chemical_formula_sum            'C15 H10 N2 O2'
_chemical_formula_weight         250.25
_chemical_compound_source        'synthesis as described'

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14


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

_cell_length_a                   14.4594(15)
_cell_length_b                   5.6092(6)
_cell_length_c                   15.0823(15)
_cell_angle_alpha                90
_cell_angle_beta                 105.035(2)
_cell_angle_gamma                90
_cell_volume                     1181.4(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    0
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             520
_exptl_special_details           ?

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

_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_type   none

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

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_reflns_av_R_equivalents  0.0157
_diffrn_reflns_av_unetI/netI     0.0142
_diffrn_reflns_number            8874
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.74
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_full        26.37
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_reflns_number_total             2407
_reflns_number_gt                2186
_reflns_threshold_expression     >2σ(I)

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

_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

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

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

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

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0545P)²+0.3272P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2407
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0457
_refine_ls_R_factor_gt           0.0417
_refine_ls_wR_factor_ref         0.1131
_refine_ls_wR_factor_gt          0.1096
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_restrained_S_all      1.073
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.191
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.036

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

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

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 1.08162(9) 0.1728(2) 0.70134(8) 0.0334(3) Uani 1 1 d . . .
C2 C 1.15384(10) 0.0170(3) 0.74545(10) 0.0421(3) Uani 1 1 d . . .
H2 H 1.1686 -0.1156 0.7147 0.05 Uiso 1 1 calc R . .
C3 C 1.20307(10) 0.0608(3) 0.83478(10) 0.0475(4) Uani 1 1 d . . .
H3 H 1.2511 -0.0435 0.8646 0.057 Uiso 1 1 calc R . .
C4 C 1.18198(11) 0.2591(3) 0.88121(10) 0.0500(4) Uani 1 1 d . . .
H4 H 1.2172 0.2894 0.9411 0.06 Uiso 1 1 calc R . .
C5 C 1.10959(11) 0.4099(3) 0.83913(9) 0.0456(4) Uani 1 1 d . . .
H5 H 1.0951 0.541 0.8708 0.055 Uiso 1 1 calc R . .
C6 C 1.05711(9) 0.3676(2) 0.74839(9) 0.0352(3) Uani 1 1 d . . .
C7 C 0.93545(9) 0.4720(2) 0.62382(9) 0.0345(3) Uani 1 1 d . . .
C8 C 0.96156(9) 0.2871(2) 0.56532(9) 0.0337(3) Uani 1 1 d . . .
C9 C 0.84971(9) 0.6269(2) 0.58141(9) 0.0367(3) Uani 1 1 d . . .
C10 C 0.75698(9) 0.5693(2) 0.60110(8) 0.0346(3) Uani 1 1 d . . .
C11 C 0.74393(11) 0.3664(3) 0.64908(10) 0.0450(3) Uani 1 1 d . . .
H11 H 0.7943 0.2604 0.67 0.054 Uiso 1 1 calc R . .
C12 C 0.65573(12) 0.3218(3) 0.66583(12) 0.0567(4) Uani 1 1 d . . .
H12 H 0.647 0.1853 0.6977 0.068 Uiso 1 1 calc R . .
C13 C 0.58152(12) 0.4777(4) 0.63567(13) 0.0626(5) Uani 1 1 d . . .
H13 H 0.5228 0.448 0.6479 0.075 Uiso 1 1 calc R . .
C14 C 0.59347(12) 0.6787(4) 0.58716(14) 0.0658(5) Uani 1 1 d . . .
H14 H 0.5426 0.7833 0.566 0.079 Uiso 1 1 calc R . .
C15 C 0.68077(11) 0.7242(3) 0.57006(11) 0.0494(4) Uani 1 1 d . . .
H15 H 0.6887 0.86 0.5374 0.059 Uiso 1 1 calc R . .
N1 N 0.98002(8) 0.5129(2) 0.70820(7) 0.0393(3) Uani 1 1 d . . .
N2 N 1.03189(8) 0.1401(2) 0.61075(7) 0.0365(3) Uani 1 1 d . . .
H2A H 1.0465 0.0197 0.5818 0.044 Uiso 1 1 calc R . .
O1 O 0.85849(8) 0.7934(2) 0.53355(9) 0.0641(4) Uani 1 1 d . . .
O2 O 0.92093(7) 0.26739(18) 0.48309(6) 0.0419(3) Uani 1 1 d . . .



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

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N2 1.3812(16) . ?
C1 C2 1.3916(19) . ?
C1 C6 1.3977(19) . ?
C2 C3 1.373(2) . ?
C2 H2 0.93 . ?
C3 C4 1.390(2) . ?
C3 H3 0.93 . ?
C4 C5 1.367(2) . ?
C4 H4 0.93 . ?
C5 C6 1.4023(18) . ?
C5 H5 0.93 . ?
C6 N1 1.3870(17) . ?
C7 N1 1.2892(16) . ?
C7 C8 1.4730(18) . ?
C7 C9 1.5130(18) . ?
C8 O2 1.2319(15) . ?
C8 N2 1.3496(17) . ?
C9 O1 1.2072(17) . ?
C9 C10 1.4822(18) . ?
C10 C15 1.3860(19) . ?
C10 C11 1.3876(19) . ?
C11 C12 1.386(2) . ?
C11 H11 0.93 . ?
C12 C13 1.367(3) . ?
C12 H12 0.93 . ?
C13 C14 1.379(3) . ?
C13 H13 0.93 . ?
C14 C15 1.376(2) . ?
C14 H14 0.93 . ?
C15 H15 0.93 . ?
N2 H2A 0.86 . ?

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 C1 C2 121.53(12) . . ?
N2 C1 C6 118.07(12) . . ?
C2 C1 C6 120.40(12) . . ?
C3 C2 C1 119.36(13) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C2 C3 C4 120.81(14) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C5 C4 C3 120.19(13) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C4 C5 C6 120.25(14) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
N1 C6 C1 121.22(11) . . ?
N1 C6 C5 119.82(12) . . ?
C1 C6 C5 118.91(12) . . ?
N1 C7 C8 125.20(12) . . ?
N1 C7 C9 117.39(12) . . ?
C8 C7 C9 117.41(11) . . ?
O2 C8 N2 123.79(12) . . ?
O2 C8 C7 122.46(12) . . ?
N2 C8 C7 113.74(11) . . ?
O1 C9 C10 121.96(12) . . ?
O1 C9 C7 119.69(12) . . ?
C10 C9 C7 118.34(11) . . ?
C15 C10 C11 119.12(13) . . ?
C15 C10 C9 118.49(12) . . ?
C11 C10 C9 122.39(12) . . ?
C12 C11 C10 119.95(14) . . ?
C12 C11 H11 120 . . ?
C10 C11 H11 120 . . ?
C13 C12 C11 120.26(16) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C12 C13 C14 120.25(15) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C15 C14 C13 119.89(16) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C14 C15 C10 120.53(15) . . ?
C14 C15 H15 119.7 . . ?
C10 C15 H15 119.7 . . ?
C7 N1 C6 117.78(11) . . ?
C8 N2 C1 123.46(11) . . ?
C8 N2 H2A 118.3 . . ?
C1 N2 H2A 118.3 . . ?

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
N2 C1 C2 C3 178.16(13) . . . . ?
C6 C1 C2 C3 -2.2(2) . . . . ?
C1 C2 C3 C4 -0.4(2) . . . . ?
C2 C3 C4 C5 2.0(2) . . . . ?
C3 C4 C5 C6 -1.0(2) . . . . ?
N2 C1 C6 N1 5.28(19) . . . . ?
C2 C1 C6 N1 -174.38(12) . . . . ?
N2 C1 C6 C5 -177.20(12) . . . . ?
C2 C1 C6 C5 3.1(2) . . . . ?
C4 C5 C6 N1 176.02(14) . . . . ?
C4 C5 C6 C1 -1.5(2) . . . . ?
N1 C7 C8 O2 -174.35(13) . . . . ?
C9 C7 C8 O2 5.41(19) . . . . ?
N1 C7 C8 N2 7.11(19) . . . . ?
C9 C7 C8 N2 -173.13(11) . . . . ?
N1 C7 C9 O1 99.06(17) . . . . ?
C8 C7 C9 O1 -80.72(17) . . . . ?
N1 C7 C9 C10 -80.36(16) . . . . ?
C8 C7 C9 C10 99.86(14) . . . . ?
O1 C9 C10 C15 -5.8(2) . . . . ?
C7 C9 C10 C15 173.64(13) . . . . ?
O1 C9 C10 C11 174.07(15) . . . . ?
C7 C9 C10 C11 -6.53(19) . . . . ?
C15 C10 C11 C12 -0.4(2) . . . . ?
C9 C10 C11 C12 179.77(14) . . . . ?
C10 C11 C12 C13 -0.3(3) . . . . ?
C11 C12 C13 C14 1.0(3) . . . . ?
C12 C13 C14 C15 -0.8(3) . . . . ?
C13 C14 C15 C10 0.1(3) . . . . ?
C11 C10 C15 C14 0.5(2) . . . . ?
C9 C10 C15 C14 -179.65(15) . . . . ?
C8 C7 N1 C6 -2.0(2) . . . . ?
C9 C7 N1 C6 178.28(11) . . . . ?
C1 C6 N1 C7 -4.44(19) . . . . ?
C5 C6 N1 C7 178.06(13) . . . . ?
O2 C8 N2 C1 175.40(12) . . . . ?
C7 C8 N2 C1 -6.08(18) . . . . ?
C2 C1 N2 C8 -179.85(13) . . . . ?
C6 C1 N2 C8 0.49(19) . . . . ?

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
N2 H2A O2 0.86 2 2.8624(15) 178.2 3_756

loop_
_publcif_info_exptl_table_extra_item
sin_theta_over_lambda_max

loop_
_publcif_info_exptl_table_header_item
?
