# 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_se1202
_database_code_depnum_ccdc_archive 'CCDC 1418634'
_audit_update_record             
;
2015-08-13 deposited with the CCDC.
2015-09-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            lawsone-bipyridyl
_chemical_formula_moiety         '2(C10 H6 O3), C10 H8 N2'
_chemical_formula_sum            'C30 H20 N2 O6'
_chemical_melting_point          456.9

_exptl_crystal_description       block
_exptl_crystal_colour            orange

_diffrn_ambient_temperature      180(2)
_chemical_formula_weight         504.48

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   'P 21/n'
_symmetry_int_tables_number      14
_chemical_absolute_configuration ?
_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                   10.6360(3)
_cell_length_b                   4.7798(1)
_cell_length_c                   23.0987(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.131(2)
_cell_angle_gamma                90.00
_cell_volume                     1167.57(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    3634
_cell_measurement_theta_min      1.00
_cell_measurement_theta_max      27.48
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.435
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             524
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.904
_exptl_absorpt_correction_T_max  0.998
_exptl_absorpt_process_details   
;
multi-scan from symmetry-related measurements 
 Sortav (Blessing 1995)
;

_exptl_special_details           
; 
 The -OH hydrogen atom was located and its position was refined
 satisfactorily.
;
_diffrn_radiation_probe          ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'Thin slice ω and φ scans'
_diffrn_reflns_number            6685
_diffrn_reflns_av_R_equivalents  0.0337
_diffrn_reflns_av_sigmaI/netI    0.0587
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         3.55
_diffrn_reflns_theta_max         27.48
_reflns_number_total             2626
_reflns_number_gt                1623
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Collect (Nonius B.V. 1998)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
;
 HKL Denzo and Scalepack (Otwinowski & Minor 1997)
;
_computing_structure_solution    'SIR-92 (Altomare et al. 1994)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick 1997)'

_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)+(0.0546P)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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2626
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0634
_refine_ls_R_factor_gt           0.0390
_refine_ls_wR_factor_ref         0.0960
_refine_ls_wR_factor_gt          0.0920
_refine_ls_goodness_of_fit_ref   0.905
_refine_ls_restrained_S_all      0.905
_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 0.81421(8) 0.0814(2) 0.15735(4) 0.0413(3) Uani 1 1 d . . .
O2 O 0.93377(8) 0.19587(19) 0.06175(4) 0.0424(3) Uani 1 1 d . . .
H2 H 0.8704 0.2718 0.0739 0.051 Uiso 1 1 calc R . .
O3 O 1.23640(8) -0.4759(2) 0.12303(4) 0.0460(3) Uani 1 1 d . . .
C1 C 0.90989(11) -0.0524(3) 0.15086(5) 0.0313(3) Uani 1 1 d . . .
C2 C 0.97814(11) -0.0013(3) 0.09890(5) 0.0322(3) Uani 1 1 d . . .
C3 C 1.08094(11) -0.1518(3) 0.08943(6) 0.0349(3) Uani 1 1 d . . .
H3 H 1.1181 -0.1230 0.0543 0.042 Uiso 1 1 calc R . .
C4 C 1.13702(11) -0.3555(3) 0.13063(6) 0.0341(3) Uani 1 1 d . . .
C5 C 1.07179(11) -0.4142(3) 0.18335(5) 0.0309(3) Uani 1 1 d . . .
C6 C 1.12056(12) -0.6139(3) 0.22335(6) 0.0378(3) Uani 1 1 d . . .
H6 H 1.1953 -0.7129 0.2170 0.045 Uiso 1 1 calc R . .
C7 C 1.06033(12) -0.6690(3) 0.27242(6) 0.0425(4) Uani 1 1 d . . .
H7 H 1.0941 -0.8051 0.2998 0.051 Uiso 1 1 calc R . .
C8 C 0.95095(13) -0.5263(3) 0.28171(6) 0.0425(4) Uani 1 1 d . . .
H8 H 0.9098 -0.5655 0.3153 0.051 Uiso 1 1 calc R . .
C9 C 0.90119(12) -0.3262(3) 0.24215(6) 0.0380(3) Uani 1 1 d . . .
H9 H 0.8262 -0.2284 0.2487 0.046 Uiso 1 1 calc R . .
C10 C 0.96171(11) -0.2695(3) 0.19285(5) 0.0309(3) Uani 1 1 d . . .
N1 N 0.73640(9) 0.5201(2) 0.05762(5) 0.0376(3) Uani 1 1 d . . .
C11 C 0.63037(13) 0.5585(3) 0.08281(6) 0.0415(4) Uani 1 1 d . . .
H11 H 0.6193 0.4537 0.1168 0.050 Uiso 1 1 calc R . .
C12 C 0.53615(13) 0.7422(3) 0.06209(6) 0.0376(4) Uani 1 1 d . . .
H12 H 0.4626 0.7621 0.0817 0.045 Uiso 1 1 calc R . .
C13 C 0.54934(11) 0.8987(3) 0.01214(5) 0.0315(3) Uani 1 1 d . . .
C14 C 0.65842(12) 0.8537(3) -0.01443(6) 0.0417(4) Uani 1 1 d . . .
H14 H 0.6714 0.9515 -0.0491 0.050 Uiso 1 1 calc R . .
C15 C 0.74810(13) 0.6669(3) 0.00955(6) 0.0422(4) Uani 1 1 d . . .
H15 H 0.8224 0.6415 -0.0093 0.051 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 1.2245(14) . ?
O2 C2 1.3269(14) . ?
O2 H2 0.8400 . ?
O3 C4 1.2325(14) . ?
C1 C10 1.4857(18) . ?
C1 C2 1.4876(18) . ?
C2 C3 1.3463(17) . ?
C3 C4 1.4449(19) . ?
C3 H3 0.9500 . ?
C4 C5 1.4912(18) . ?
C5 C6 1.3897(18) . ?
C5 C10 1.3973(17) . ?
C6 C7 1.3856(19) . ?
C6 H6 0.9500 . ?
C7 C8 1.3851(19) . ?
C7 H7 0.9500 . ?
C8 C9 1.3880(19) . ?
C8 H8 0.9500 . ?
C9 C10 1.3931(18) . ?
C9 H9 0.9500 . ?
N1 C15 1.3303(17) . ?
N1 C11 1.3357(17) . ?
C11 C12 1.3791(19) . ?
C11 H11 0.9500 . ?
C12 C13 1.3946(18) . ?
C12 H12 0.9500 . ?
C13 C14 1.3859(18) . ?
C13 C13 1.493(2) 3_675 ?
C14 C15 1.3789(19) . ?
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
C2 O2 H2 109.5 . . ?
O1 C1 C10 122.68(12) . . ?
O1 C1 C2 119.77(12) . . ?
C10 C1 C2 117.55(11) . . ?
O2 C2 C3 120.89(12) . . ?
O2 C2 C1 117.91(11) . . ?
C3 C2 C1 121.20(12) . . ?
C2 C3 C4 122.57(12) . . ?
C2 C3 H3 118.7 . . ?
C4 C3 H3 118.7 . . ?
O3 C4 C3 121.39(12) . . ?
O3 C4 C5 120.61(12) . . ?
C3 C4 C5 118.00(11) . . ?
C6 C5 C10 119.67(12) . . ?
C6 C5 C4 119.94(12) . . ?
C10 C5 C4 120.38(12) . . ?
C7 C6 C5 120.14(13) . . ?
C7 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C8 C7 C6 120.16(13) . . ?
C8 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
C7 C8 C9 120.33(13) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 H8 119.8 . . ?
C8 C9 C10 119.68(13) . . ?
C8 C9 H9 120.2 . . ?
C10 C9 H9 120.2 . . ?
C9 C10 C5 120.01(12) . . ?
C9 C10 C1 119.86(11) . . ?
C5 C10 C1 120.12(12) . . ?
C15 N1 C11 116.72(12) . . ?
N1 C11 C12 123.53(13) . . ?
N1 C11 H11 118.2 . . ?
C12 C11 H11 118.2 . . ?
C11 C12 C13 119.67(13) . . ?
C11 C12 H12 120.2 . . ?
C13 C12 H12 120.2 . . ?
C14 C13 C12 116.49(12) . . ?
C14 C13 C13 121.51(15) . 3_675 ?
C12 C13 C13 122.00(14) . 3_675 ?
C15 C14 C13 119.90(13) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
N1 C15 C14 123.67(13) . . ?
N1 C15 H15 118.2 . . ?
C14 C15 H15 118.2 . . ?

_diffrn_measured_fraction_theta_max 0.980
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.980
_refine_diff_density_max         0.144
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.041

_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
####################################################################### 
# 
# 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_se1203
_database_code_depnum_ccdc_archive 'CCDC 1418635'
_audit_update_record             
;
2015-08-13 deposited with the CCDC.
2015-09-03 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            lawsone-ethylenebipyridine
_chemical_formula_moiety         'C12 H12 N2 2+, 2(C10 H5 O3 1-)'
_chemical_formula_sum            'C32 H22 N2 O6'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
_chemical_melting_point          283.1

_exptl_crystal_description       block
_exptl_crystal_colour            colourless

_diffrn_ambient_temperature      180(2)
_chemical_formula_weight         530.52

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   'P 21/n'
_symmetry_int_tables_number      14
_chemical_absolute_configuration ?
_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                   3.8157(1)
_cell_length_b                   28.0772(7)
_cell_length_c                   11.2326(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.542(2)
_cell_angle_gamma                90.00
_cell_volume                     1195.56(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    10367
_cell_measurement_theta_min      1.00
_cell_measurement_theta_max      32.03
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.474
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             552
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.930
_exptl_absorpt_correction_T_max  0.996
_exptl_absorpt_process_details   
;
multi-scan from symmetry-related measurements 
 Sortav (Blessing 1995)
;

_exptl_special_details           
; 
 
;
_diffrn_radiation_probe          ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'Thin slice ω and φ scans'
_diffrn_reflns_number            10270
_diffrn_reflns_av_R_equivalents  0.0505
_diffrn_reflns_av_sigmaI/netI    0.0837
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_k_max       41
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.65
_diffrn_reflns_theta_max         32.00
_reflns_number_total             4108
_reflns_number_gt                2319
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Collect (Nonius B.V. 1998)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
;
 HKL Denzo and Scalepack (Otwinowski & Minor 1997)
;
_computing_structure_solution    'SIR-92 (Altomare et al. 1994)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick 1997)'

_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)+(0.0588P)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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4108
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1185
_refine_ls_R_factor_gt           0.0578
_refine_ls_wR_factor_ref         0.1408
_refine_ls_wR_factor_gt          0.1227
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_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 0.2355(3) 0.06894(5) -0.14389(10) 0.0288(3) Uani 1 1 d . . .
H1 H 0.1734 0.0787 -0.0748 0.035 Uiso 1 1 calc R . .
C11 C 0.3043(4) 0.02320(6) -0.16033(13) 0.0300(4) Uani 1 1 d . . .
H11 H 0.2872 0.0014 -0.0966 0.036 Uiso 1 1 calc R . .
C12 C 0.3998(4) 0.00662(6) -0.26751(12) 0.0290(4) Uani 1 1 d . . .
H12 H 0.4518 -0.0262 -0.2767 0.035 Uiso 1 1 calc R . .
C13 C 0.4201(4) 0.03815(6) -0.36239(12) 0.0250(3) Uani 1 1 d . . .
C14 C 0.3505(4) 0.08605(6) -0.34197(13) 0.0308(4) Uani 1 1 d . . .
H14 H 0.3652 0.1089 -0.4037 0.037 Uiso 1 1 calc R . .
C15 C 0.2605(5) 0.10017(6) -0.23225(13) 0.0316(4) Uani 1 1 d . . .
H15 H 0.2151 0.1329 -0.2190 0.038 Uiso 1 1 calc R . .
C16 C 0.5088(4) 0.02244(6) -0.48047(12) 0.0276(3) Uani 1 1 d . . .
H16 H 0.5842 0.0460 -0.5326 0.041 Uiso 1 1 calc R . .
O1 O -0.1604(3) 0.14997(4) -0.04073(9) 0.0347(3) Uani 1 1 d . . .
O2 O 0.1356(3) 0.07422(4) 0.07792(9) 0.0349(3) Uani 1 1 d . . .
O3 O -0.2132(3) 0.13767(4) 0.43300(9) 0.0363(3) Uani 1 1 d . . .
C1 C -0.1651(4) 0.14912(5) 0.06809(12) 0.0240(3) Uani 1 1 d . . .
C2 C -0.0094(4) 0.10695(6) 0.13799(12) 0.0260(3) Uani 1 1 d . . .
C3 C -0.0290(4) 0.10515(6) 0.25909(12) 0.0266(3) Uani 1 1 d . . .
H3 H 0.0700 0.0784 0.3023 0.032 Uiso 1 1 calc R . .
C4 C -0.1896(4) 0.14120(6) 0.32368(12) 0.0258(3) Uani 1 1 d . . .
C5 C -0.3281(4) 0.18484(5) 0.25769(12) 0.0230(3) Uani 1 1 d . . .
C6 C -0.4678(4) 0.22223(6) 0.31797(12) 0.0273(4) Uani 1 1 d . . .
H6 H -0.4868 0.2195 0.4013 0.033 Uiso 1 1 calc R . .
C7 C -0.5800(4) 0.26357(6) 0.25779(13) 0.0288(4) Uani 1 1 d . . .
H7 H -0.6701 0.2892 0.3003 0.035 Uiso 1 1 calc R . .
C8 C -0.5610(4) 0.26759(6) 0.13536(13) 0.0290(4) Uani 1 1 d . . .
H8 H -0.6353 0.2961 0.0943 0.035 Uiso 1 1 calc R . .
C9 C -0.4331(4) 0.22988(5) 0.07340(13) 0.0267(3) Uani 1 1 d . . .
H9 H -0.4265 0.2322 -0.0107 0.032 Uiso 1 1 calc R . .
C10 C -0.3139(4) 0.18848(5) 0.13378(11) 0.0227(3) Uani 1 1 d . . .


_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 C11 1.328(2) . ?
N1 C15 1.3359(19) . ?
N1 H1 0.8800 . ?
C11 C12 1.378(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.394(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.395(2) . ?
C13 C16 1.473(2) . ?
C14 C15 1.375(2) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 C16 1.333(3) 3_654 ?
C16 H16 0.9500 . ?
O1 C1 1.2247(16) . ?
O2 C2 1.3001(18) . ?
O3 C4 1.2454(17) . ?
C1 C10 1.478(2) . ?
C1 C2 1.505(2) . ?
C2 C3 1.3718(18) . ?
C3 C4 1.424(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.497(2) . ?
C5 C6 1.388(2) . ?
C5 C10 1.4028(18) . ?
C6 C7 1.386(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.390(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.386(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.396(2) . ?
C9 H9 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
C11 N1 C15 119.97(14) . . ?
C11 N1 H1 120.0 . . ?
C15 N1 H1 120.0 . . ?
N1 C11 C12 121.63(15) . . ?
N1 C11 H11 119.2 . . ?
C12 C11 H11 119.2 . . ?
C11 C12 C13 119.76(15) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
C12 C13 C14 117.28(14) . . ?
C12 C13 C16 122.43(14) . . ?
C14 C13 C16 120.28(13) . . ?
C15 C14 C13 119.81(15) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
N1 C15 C14 121.53(15) . . ?
N1 C15 H15 119.2 . . ?
C14 C15 H15 119.2 . . ?
C16 C16 C13 124.82(19) 3_654 . ?
C16 C16 H16 117.6 3_654 . ?
C13 C16 H16 117.6 . . ?
O1 C1 C10 122.27(14) . . ?
O1 C1 C2 119.09(14) . . ?
C10 C1 C2 118.63(12) . . ?
O2 C2 C3 124.28(14) . . ?
O2 C2 C1 116.83(12) . . ?
C3 C2 C1 118.89(14) . . ?
C2 C3 C4 123.68(14) . . ?
C2 C3 H3 118.2 . . ?
C4 C3 H3 118.2 . . ?
O3 C4 C3 121.98(14) . . ?
O3 C4 C5 119.48(14) . . ?
C3 C4 C5 118.53(13) . . ?
C6 C5 C10 119.30(14) . . ?
C6 C5 C4 120.74(13) . . ?
C10 C5 C4 119.96(14) . . ?
C7 C6 C5 120.65(14) . . ?
C7 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C6 C7 C8 120.17(15) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 H7 119.9 . . ?
C9 C8 C7 119.72(15) . . ?
C9 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
C8 C9 C10 120.40(14) . . ?
C8 C9 H9 119.8 . . ?
C10 C9 H9 119.8 . . ?
C9 C10 C5 119.71(14) . . ?
C9 C10 C1 120.17(13) . . ?
C5 C10 C1 120.10(13) . . ?

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        32.00
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.232
_refine_diff_density_min         -0.409
_refine_diff_density_rms         0.057

####################################################################### 
# 
# 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_se1205
_database_code_depnum_ccdc_archive 'CCDC 1418636'
_audit_update_record             
;
2015-08-14 deposited with the CCDC.
2015-09-03 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_THETM01_se1205              
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: The diffraction limit was low due to the low quality of the crystal.
;
_vrf_REFNR01_se1205              
;
PROBLEM: Ratio of reflections to parameters is < 6 for a
RESPONSE: The diffraction from the crystal was weak and the number of datapoints was low.
;
_vrf_PLAT089_se1205              
;
PROBLEM: Poor Data / Parameter Ratio (Zmax &lt; 18) ........       5.10 Note
RESPONSE: The diffraction from the crystal was weak and the number of datapoints was low.
;
_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            lawsone-trimethylenebipyridine
_chemical_formula_moiety         'C13 H14 N2, 2(C10 H6 O3)'
_chemical_formula_sum            'C33 H26 N2 O6'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methanol'
_chemical_melting_point          428.8

_exptl_crystal_description       needle
_exptl_crystal_colour            orange

_diffrn_ambient_temperature      180(2)
_chemical_formula_weight         546.56

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   'F d d 2'
_symmetry_int_tables_number      43
_chemical_absolute_configuration ?
_symmetry_space_group_name_Hall  'F 2 -2d'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'x+1/4, -y+1/4, z+1/4'
'-x+1/4, y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'x+1/4, -y+3/4, z+3/4'
'-x+1/4, y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'x+3/4, -y+1/4, z+3/4'
'-x+3/4, y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'x+3/4, -y+3/4, z+1/4'
'-x+3/4, y+3/4, z+1/4'

_cell_length_a                   22.5402(9)
_cell_length_b                   50.511(2)
_cell_length_c                   4.6451(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     5288.6(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    2847
_cell_measurement_theta_min      1.00
_cell_measurement_theta_max      22.46
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2288
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.948
_exptl_absorpt_correction_T_max  0.999
_exptl_absorpt_process_details   
;
multi-scan from symmetry-related measurements 
 Sortav (Blessing 1995)
;

_exptl_special_details           
; 
 Small needle-like crystals, poorly diffracting.  Theta(max)=22.5deg.
 Poor parameter/data ratio.
 589 Friedel pairs were averaged for the refinement.  The -OH hydrogen
 atom was located and its position was refined satisfactorily.
;
_diffrn_radiation_probe          ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'Thin slice ω and φ scans'
_diffrn_reflns_number            3385
_diffrn_reflns_av_R_equivalents  0.0292
_diffrn_reflns_av_sigmaI/netI    0.0323
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -50
_diffrn_reflns_limit_k_max       54
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_limit_l_max       4
_diffrn_reflns_theta_min         3.62
_diffrn_reflns_theta_max         22.44
_reflns_number_total             972
_reflns_number_gt                915
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Collect (Nonius B.V. 1998)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
;
 HKL Denzo and Scalepack (Otwinowski & Minor 1997)
;
_computing_structure_solution    'SIR-92 (Altomare et al. 1994)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick 1997)'

_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)+(0.0329P)²+2.5971P] 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     SHELXL
_refine_ls_extinction_coef       0.0022(3)
_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   0.9(18)
_refine_ls_number_reflns         972
_refine_ls_number_parameters     193
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0293
_refine_ls_R_factor_gt           0.0261
_refine_ls_wR_factor_ref         0.0652
_refine_ls_wR_factor_gt          0.0630
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_restrained_S_all      1.082
_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 0.27823(7) 0.08488(3) 1.1020(5) 0.0466(5) Uani 1 1 d . . .
O2 O 0.21725(8) 0.04236(3) 0.9135(4) 0.0463(5) Uani 1 1 d . . .
H2 H 0.2587(12) 0.0474(5) 0.833(7) 0.056 Uiso 1 1 d . . .
O3 O 0.06547(8) 0.06382(4) 1.5587(6) 0.0611(6) Uani 1 1 d . . .
C1 C 0.22978(10) 0.08086(5) 1.2110(6) 0.0357(6) Uani 1 1 d . . .
C2 C 0.19417(10) 0.05745(5) 1.1167(6) 0.0367(6) Uani 1 1 d . . .
C3 C 0.14075(11) 0.05220(5) 1.2353(6) 0.0419(7) Uani 1 1 d . . .
H3 H 0.1197 0.0369 1.1734 0.050 Uiso 1 1 calc R . .
C4 C 0.11451(11) 0.06885(5) 1.4519(6) 0.0426(7) Uani 1 1 d . . .
C5 C 0.14740(10) 0.09307(5) 1.5452(6) 0.0354(6) Uani 1 1 d . . .
C6 C 0.12276(11) 0.11040(5) 1.7432(6) 0.0433(7) Uani 1 1 d . . .
H6 H 0.0846 0.1069 1.8205 0.052 Uiso 1 1 calc R . .
C7 C 0.15308(11) 0.13275(5) 1.8291(7) 0.0446(7) Uani 1 1 d . . .
H7 H 0.1355 0.1447 1.9621 0.053 Uiso 1 1 calc R . .
C8 C 0.20934(11) 0.13782(5) 1.7213(6) 0.0434(7) Uani 1 1 d . . .
H8 H 0.2306 0.1530 1.7834 0.052 Uiso 1 1 calc R . .
C9 C 0.23439(11) 0.12078(5) 1.5242(6) 0.0400(7) Uani 1 1 d . . .
H9 H 0.2729 0.1243 1.4508 0.048 Uiso 1 1 calc R . .
C10 C 0.20359(10) 0.09842(5) 1.4318(5) 0.0342(6) Uani 1 1 d . . .
N1 N 0.31421(9) 0.04312(4) 0.6303(5) 0.0402(6) Uani 1 1 d . . .
C11 C 0.36454(11) 0.05691(5) 0.6043(7) 0.0437(7) Uani 1 1 d . . .
H11 H 0.3687 0.0729 0.7107 0.052 Uiso 1 1 calc R . .
C12 C 0.41066(11) 0.04897(5) 0.4294(7) 0.0427(7) Uani 1 1 d . . .
H12 H 0.4458 0.0593 0.4182 0.051 Uiso 1 1 calc R . .
C13 C 0.40554(10) 0.02582(5) 0.2697(6) 0.0362(6) Uani 1 1 d . . .
C14 C 0.35302(11) 0.01172(5) 0.2980(6) 0.0397(7) Uani 1 1 d . . .
H14 H 0.3472 -0.0042 0.1929 0.048 Uiso 1 1 calc R . .
C15 C 0.30970(11) 0.02086(5) 0.4776(6) 0.0428(7) Uani 1 1 d . . .
H15 H 0.2743 0.0108 0.4948 0.051 Uiso 1 1 calc R . .
C16 C 0.45514(10) 0.01526(5) 0.0880(6) 0.0419(7) Uani 1 1 d . . .
H16A H 0.4754 0.0301 -0.0099 0.050 Uiso 1 1 calc R . .
H16B H 0.4388 0.0034 -0.0617 0.050 Uiso 1 1 calc R . .
C17 C 0.5000 0.0000 0.2725(9) 0.0421(9) Uani 1 2 d S . .
H17 H 0.4771(11) -0.0134(5) 0.411(7) 0.051 Uiso 1 1 d . . .


_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 1.221(3) . ?
O2 C2 1.320(3) . ?
O2 H2 1.04(3) . ?
O3 C4 1.238(3) . ?
C1 C10 1.479(4) . ?
C1 C2 1.494(4) . ?
C2 C3 1.350(3) . ?
C3 C4 1.438(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.495(4) . ?
C5 C6 1.386(4) . ?
C5 C10 1.398(3) . ?
C6 C7 1.378(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.387(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.378(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.394(3) . ?
C9 H9 0.9500 . ?
N1 C15 1.333(3) . ?
N1 C11 1.337(3) . ?
C11 C12 1.379(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.390(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.388(3) . ?
C13 C16 1.499(4) . ?
C14 C15 1.365(4) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 C17 1.533(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C16 1.533(3) 2_655 ?
C17 H17 1.07(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O2 H2 118.0(16) . . ?
O1 C1 C10 123.0(2) . . ?
O1 C1 C2 119.4(2) . . ?
C10 C1 C2 117.6(2) . . ?
O2 C2 C3 122.0(2) . . ?
O2 C2 C1 117.0(2) . . ?
C3 C2 C1 121.0(3) . . ?
C2 C3 C4 122.5(2) . . ?
C2 C3 H3 118.8 . . ?
C4 C3 H3 118.8 . . ?
O3 C4 C3 121.8(2) . . ?
O3 C4 C5 119.6(3) . . ?
C3 C4 C5 118.5(2) . . ?
C6 C5 C10 119.4(2) . . ?
C6 C5 C4 120.7(2) . . ?
C10 C5 C4 119.9(2) . . ?
C7 C6 C5 120.7(2) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C6 C7 C8 120.0(3) . . ?
C6 C7 H7 120.0 . . ?
C8 C7 H7 120.0 . . ?
C9 C8 C7 119.9(2) . . ?
C9 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
C8 C9 C10 120.5(2) . . ?
C8 C9 H9 119.8 . . ?
C10 C9 H9 119.8 . . ?
C9 C10 C5 119.4(2) . . ?
C9 C10 C1 120.1(2) . . ?
C5 C10 C1 120.5(2) . . ?
C15 N1 C11 117.1(2) . . ?
N1 C11 C12 122.8(3) . . ?
N1 C11 H11 118.6 . . ?
C12 C11 H11 118.6 . . ?
C11 C12 C13 119.8(2) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
C14 C13 C12 116.9(2) . . ?
C14 C13 C16 120.5(2) . . ?
C12 C13 C16 122.6(2) . . ?
C15 C14 C13 119.7(2) . . ?
C15 C14 H14 120.2 . . ?
C13 C14 H14 120.2 . . ?
N1 C15 C14 123.8(2) . . ?
N1 C15 H15 118.1 . . ?
C14 C15 H15 118.1 . . ?
C13 C16 C17 110.8(2) . . ?
C13 C16 H16A 109.5 . . ?
C17 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
C17 C16 H16B 109.5 . . ?
H16A C16 H16B 108.1 . . ?
C16 C17 C16 112.0(3) 2_655 . ?
C16 C17 H17 109.6(15) 2_655 . ?
C16 C17 H17 109.7(14) . . ?

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        22.44
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.099
_refine_diff_density_min         -0.097
_refine_diff_density_rms         0.025

####################################################################### 
# 
# 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 
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data_conor_nq-hp
_database_code_depnum_ccdc_archive 'CCDC 1418637'
_audit_update_record             
;
2015-08-13 deposited with the CCDC.
2015-09-03 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            lawsone-hydroxypyridine
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H11 N O4'
_chemical_melting_point          420.9

_exptl_crystal_description       Parallelepiped
_exptl_crystal_colour            Colourless
_diffrn_ambient_temperature      299.3(6)
_chemical_formula_weight         269.25

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, -y+1/2, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, -z-1/2'

_cell_length_a                   13.6937(12)
_cell_length_b                   5.1534(3)
_cell_length_c                   17.5288(12)
_cell_angle_alpha                90
_cell_angle_beta                 92.329(7)
_cell_angle_gamma                90
_cell_volume                     1235.97(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    299.3(6)
_cell_measurement_reflns_used    1297
_cell_measurement_theta_min      4.5840
_cell_measurement_theta_max      29.1660
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.447
_exptl_crystal_F_000             560
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_exptl_absorpt_coefficient_mu    0.106
_shelx_estimated_absorpt_T_min   0.949
_shelx_estimated_absorpt_T_max   0.979
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.72226
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
crysalispro, agilent technologies,
version 1.171.37.35 (release 13-08-2014 crysalis171 .net)
(compiled aug 13 2014,18:06:01)
empirical absorption correction using spherical harmonics,
 implemented in scale3 abspack scaling algorithm.
;
_diffrn_radiation_probe          ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.1048
_diffrn_reflns_number            5890
_diffrn_reflns_av_unetI/netI     0.0370
_diffrn_reflns_av_R_equivalents  0.0201
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.704
_diffrn_reflns_theta_max         29.196
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.865
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.865
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.865
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2880
_reflns_number_gt                1948
_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       
;
'Wed Feb 25 20:23:53 2015'
;
_computing_cell_refinement       
;
'Wed Feb 25 20:23:53 2015'
;
_computing_data_reduction        
;
'Wed Feb 25 20:23:53 2015'
;
_computing_structure_solution    SHELXT
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    OSCAIL
_computing_publication_material  ?
_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)+(0.0521P)²+0.2368P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2880
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0748
_refine_ls_R_factor_gt           0.0445
_refine_ls_wR_factor_ref         0.1242
_refine_ls_wR_factor_gt          0.1047
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_restrained_S_all      1.014
_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_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
O1 O 0.34130(9) 0.6404(2) 0.53957(7) 0.0487(4) Uani 1 1 d . . . . .
O2 O 0.26672(9) 0.5115(2) 0.40070(7) 0.0451(3) Uani 1 1 d . . . . .
H2 H 0.3109 0.4451 0.4270 0.059 Uiso 1 1 calc R U . . .
O3 O 0.04544(9) 1.1948(3) 0.41977(8) 0.0524(4) Uani 1 1 d . . . . .
O4 O 0.40747(9) 0.1793(2) 0.44675(7) 0.0450(3) Uani 1 1 d . . . . .
N1 N 0.49239(10) -0.1648(3) 0.40380(8) 0.0378(4) Uani 1 1 d . . . . .
H1 H 0.5194 -0.1819 0.4487 0.049 Uiso 1 1 calc R U . . .
C1 C 0.27188(12) 0.7665(3) 0.51571(9) 0.0330(4) Uani 1 1 d . . . . .
C2 C 0.22843(12) 0.7082(3) 0.43867(9) 0.0345(4) Uani 1 1 d . . . . .
C3 C 0.15456(13) 0.8515(3) 0.40847(10) 0.0406(4) Uani 1 1 d . . . . .
H3 H 0.1300 0.8123 0.3596 0.053 Uiso 1 1 calc R U . . .
C4 C 0.11176(12) 1.0648(3) 0.44921(10) 0.0373(4) Uani 1 1 d . . . . .
C5 C 0.15004(12) 1.1208(3) 0.52831(9) 0.0328(4) Uani 1 1 d . . . . .
C6 C 0.10838(13) 1.3153(3) 0.57122(11) 0.0430(4) Uani 1 1 d . . . . .
H6 H 0.0563 1.4115 0.5505 0.056 Uiso 1 1 calc R U . . .
C7 C 0.14395(15) 1.3656(4) 0.64408(11) 0.0499(5) Uani 1 1 d . . . . .
H7 H 0.1156 1.4953 0.6727 0.065 Uiso 1 1 calc R U . . .
C8 C 0.22152(16) 1.2246(4) 0.67499(11) 0.0514(5) Uani 1 1 d . . . . .
H8 H 0.2456 1.2606 0.7242 0.067 Uiso 1 1 calc R U . . .
C9 C 0.26363(14) 1.0306(4) 0.63320(10) 0.0430(4) Uani 1 1 d . . . . .
H9 H 0.3159 0.9357 0.6542 0.056 Uiso 1 1 calc R U . . .
C10 C 0.22763(12) 0.9779(3) 0.55994(9) 0.0320(4) Uani 1 1 d . . . . .
C11 C 0.42677(12) 0.0308(3) 0.39221(10) 0.0351(4) Uani 1 1 d . . . . .
C12 C 0.38433(14) 0.0472(4) 0.31692(10) 0.0427(4) Uani 1 1 d . . . . .
H12 H 0.3386 0.1761 0.3053 0.056 Uiso 1 1 calc R U . . .
C13 C 0.40937(15) -0.1214(3) 0.26188(10) 0.0461(5) Uani 1 1 d . . . . .
H13 H 0.3804 -0.1078 0.2132 0.060 Uiso 1 1 calc R U . . .
C14 C 0.47857(14) -0.3163(4) 0.27760(11) 0.0449(5) Uani 1 1 d . . . . .
H14 H 0.4969 -0.4301 0.2396 0.058 Uiso 1 1 calc R U . . .
C15 C 0.51790(13) -0.3348(3) 0.34891(10) 0.0418(4) Uani 1 1 d . . . . .
H15 H 0.5630 -0.4652 0.3607 0.054 Uiso 1 1 calc 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
O1 C1 1.2118(19) . ?
O2 C2 1.3319(19) . ?
O2 H2 0.8200 . ?
O3 C4 1.226(2) . ?
O4 C11 1.261(2) . ?
N1 C15 1.357(2) . ?
N1 C11 1.360(2) . ?
N1 H1 0.8600 . ?
C1 C10 1.481(2) . ?
C1 C2 1.484(2) . ?
C2 C3 1.344(2) . ?
C3 C4 1.448(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.490(2) . ?
C5 C6 1.389(2) . ?
C5 C10 1.389(2) . ?
C6 C7 1.373(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.379(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.380(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.384(2) . ?
C9 H9 0.9300 . ?
C11 C12 1.423(2) . ?
C12 C13 1.353(2) . ?
C12 H12 0.9300 . ?
C13 C14 1.400(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.344(2) . ?
C14 H14 0.9300 . ?
C15 H15 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
C2 O2 H2 109.5 . . ?
C15 N1 C11 124.06(15) . . ?
C15 N1 H1 118.0 . . ?
C11 N1 H1 118.0 . . ?
O1 C1 C10 123.06(15) . . ?
O1 C1 C2 119.04(15) . . ?
C10 C1 C2 117.89(14) . . ?
O2 C2 C3 121.78(16) . . ?
O2 C2 C1 117.22(14) . . ?
C3 C2 C1 120.98(15) . . ?
C2 C3 C4 122.43(16) . . ?
C2 C3 H3 118.8 . . ?
C4 C3 H3 118.8 . . ?
O3 C4 C3 121.01(16) . . ?
O3 C4 C5 120.83(16) . . ?
C3 C4 C5 118.15(15) . . ?
C6 C5 C10 119.37(16) . . ?
C6 C5 C4 120.44(15) . . ?
C10 C5 C4 120.20(14) . . ?
C7 C6 C5 120.12(17) . . ?
C7 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C6 C7 C8 120.28(17) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 H7 119.9 . . ?
C7 C8 C9 120.33(18) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 H8 119.8 . . ?
C8 C9 C10 119.61(17) . . ?
C8 C9 H9 120.2 . . ?
C10 C9 H9 120.2 . . ?
C9 C10 C5 120.28(15) . . ?
C9 C10 C1 119.49(15) . . ?
C5 C10 C1 120.22(15) . . ?
O4 C11 N1 119.61(15) . . ?
O4 C11 C12 125.23(16) . . ?
N1 C11 C12 115.15(15) . . ?
C13 C12 C11 121.17(17) . . ?
C13 C12 H12 119.4 . . ?
C11 C12 H12 119.4 . . ?
C12 C13 C14 120.62(17) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 H13 119.7 . . ?
C15 C14 C13 118.44(17) . . ?
C15 C14 H14 120.8 . . ?
C13 C14 H14 120.8 . . ?
C14 C15 N1 120.54(17) . . ?
C14 C15 H15 119.7 . . ?
N1 C15 H15 119.7 . . ?

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
O1 C1 C2 O2 2.3(2) . . . . ?
C10 C1 C2 O2 -177.62(13) . . . . ?
O1 C1 C2 C3 -176.66(16) . . . . ?
C10 C1 C2 C3 3.4(2) . . . . ?
O2 C2 C3 C4 179.58(15) . . . . ?
C1 C2 C3 C4 -1.5(3) . . . . ?
C2 C3 C4 O3 178.85(17) . . . . ?
C2 C3 C4 C5 -1.6(3) . . . . ?
O3 C4 C5 C6 2.6(3) . . . . ?
C3 C4 C5 C6 -176.92(15) . . . . ?
O3 C4 C5 C10 -177.66(16) . . . . ?
C3 C4 C5 C10 2.8(2) . . . . ?
C10 C5 C6 C7 0.2(3) . . . . ?
C4 C5 C6 C7 179.93(16) . . . . ?
C5 C6 C7 C8 0.4(3) . . . . ?
C6 C7 C8 C9 -0.5(3) . . . . ?
C7 C8 C9 C10 0.0(3) . . . . ?
C8 C9 C10 C5 0.5(3) . . . . ?
C8 C9 C10 C1 -178.97(16) . . . . ?
C6 C5 C10 C9 -0.6(2) . . . . ?
C4 C5 C10 C9 179.63(16) . . . . ?
C6 C5 C10 C1 178.86(15) . . . . ?
C4 C5 C10 C1 -0.9(2) . . . . ?
O1 C1 C10 C9 -2.6(3) . . . . ?
C2 C1 C10 C9 177.35(15) . . . . ?
O1 C1 C10 C5 177.91(16) . . . . ?
C2 C1 C10 C5 -2.1(2) . . . . ?
C15 N1 C11 O4 179.88(16) . . . . ?
C15 N1 C11 C12 0.4(2) . . . . ?
O4 C11 C12 C13 -179.85(17) . . . . ?
N1 C11 C12 C13 -0.4(3) . . . . ?
C11 C12 C13 C14 -0.4(3) . . . . ?
C12 C13 C14 C15 1.3(3) . . . . ?
C13 C14 C15 N1 -1.3(3) . . . . ?
C11 N1 C15 C14 0.5(3) . . . . ?

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
O2 H2 O1 0.82 2.24 2.6849(17) 114.4 .
O2 H2 O4 0.82 1.93 2.6779(17) 152.1 .
N1 H1 O4 0.86 2.05 2.9081(19) 172.8 3_656

_refine_diff_density_max         0.180
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.040

_symmetry_cell_setting           ?
_symmetry_space_group_name_h-m   ?
_symmetry_int_tables_number      ?
_chemical_absolute_configuration ?

_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
