# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_parentacid
_database_code_depnum_ccdc_archive 'CCDC 1435389'
_audit_update_record             
;
2015-11-05 deposited with the CCDC.
2016-01-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
Naphthalaldehydic acid cyclised isomer  15. 
;
_chemical_name_common            ?
_chemical_melting_point          433-440
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H8 O3'
_chemical_formula_weight         200.18

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

_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                   12.135(15)
_cell_length_b                   3.979(5)
_cell_length_c                   18.38(2)
_cell_angle_alpha                90
_cell_angle_beta                 91.40(3)
_cell_angle_gamma                90
_cell_volume                     887.2(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2323
_cell_measurement_theta_min      2.2
_cell_measurement_theta_max      31.1

_exptl_crystal_description       Needle
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.499
_exptl_crystal_F_000             416
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.108
_shelx_estimated_absorpt_T_min   0.948
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9478
_exptl_absorpt_correction_T_max  0.9968
_exptl_absorpt_process_details   
;   
CrystalClear-SM Expert 2.0 r11 (Rigaku, 2011) 
;
_exptl_special_details           
;

;
_diffrn_source_power             2.5
_diffrn_source_voltage           45.0
_diffrn_source_current           55.0
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           'Mo K\a'
_diffrn_source                   'Rotating Anode'
_diffrn_radiation_monochromator  Confocal
_diffrn_measurement_specimen_support Mitegen
_diffrn_detector                 CCD
_diffrn_measurement_device       
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type  
;
Rigaku Saturn724+ (2x2 bin mode)
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_reflns_number            4201
_diffrn_reflns_av_unetI/netI     0.0485
_diffrn_reflns_av_R_equivalents  0.0367
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.359
_diffrn_reflns_theta_max         27.483
_diffrn_reflns_theta_full        27.500
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             2007
_reflns_number_gt                1431
_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       
;
CrystalClear-SM Expert 2.0 r11 (Rigaku, 2011)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r11 (Rigaku, 2011)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r11 (Rigaku, 2011)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
The hydroxyl H atom was refined without restraints.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0598P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2007
_refine_ls_number_parameters     147
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0597
_refine_ls_R_factor_gt           0.0424
_refine_ls_wR_factor_ref         0.1102
_refine_ls_wR_factor_gt          0.1017
_refine_ls_goodness_of_fit_ref   0.970
_refine_ls_restrained_S_all      0.970
_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 -0.01274(8) -0.3454(3) 0.10772(5) 0.0232(3) Uani 1 1 d . . . . .
O2 O 0.06678(8) -0.0676(3) 0.19767(5) 0.0203(3) Uani 1 1 d . . . . .
O3 O 0.18147(9) -0.0014(3) 0.29799(5) 0.0226(3) Uani 1 1 d . . . . .
H3A H 0.1262(17) 0.049(5) 0.3315(10) 0.056(6) Uiso 1 1 d . . . . .
C1 C 0.15468(11) -0.0651(4) 0.08017(7) 0.0161(3) Uani 1 1 d . . . . .
C2 C 0.15028(12) -0.1512(4) 0.00742(7) 0.0196(3) Uani 1 1 d . . . . .
H2 H 0.0878 -0.2658 -0.0124 0.031(5) Uiso 1 1 calc R . . . .
C3 C 0.23934(13) -0.0681(4) -0.03740(7) 0.0214(4) Uani 1 1 d . . . . .
H3 H 0.2358 -0.1216 -0.0878 0.019(4) Uiso 1 1 calc R . . . .
C4 C 0.33068(12) 0.0893(4) -0.00836(8) 0.0213(3) Uani 1 1 d . . . . .
H4 H 0.3904 0.1403 -0.0390 0.026(4) Uiso 1 1 calc R . . . .
C5 C 0.33818(12) 0.1780(4) 0.06639(7) 0.0177(3) Uani 1 1 d . . . . .
C6 C 0.43214(12) 0.3355(4) 0.09859(8) 0.0216(4) Uani 1 1 d . . . . .
H6 H 0.4941 0.3827 0.0697 0.026(4) Uiso 1 1 calc R . . . .
C7 C 0.43489(12) 0.4207(4) 0.17102(8) 0.0220(4) Uani 1 1 d . . . . .
H7 H 0.4989 0.5234 0.1918 0.032(5) Uiso 1 1 calc R . . . .
C8 C 0.34288(12) 0.3566(4) 0.21493(7) 0.0198(3) Uani 1 1 d . . . . .
H8 H 0.3446 0.4223 0.2646 0.022(4) Uiso 1 1 calc R . . . .
C9 C 0.25114(11) 0.1995(4) 0.18583(7) 0.0163(3) Uani 1 1 d . . . . .
C10 C 0.24713(11) 0.1051(4) 0.11135(7) 0.0155(3) Uani 1 1 d . . . . .
C11 C 0.06389(12) -0.1659(4) 0.12783(7) 0.0173(3) Uani 1 1 d . . . . .
C12 C 0.15182(12) 0.1491(4) 0.23232(7) 0.0174(3) Uani 1 1 d . . . . .
H12 H 0.1185 0.3735 0.2425 0.017(4) 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 C11 1.2226(19) . ?
O2 C11 1.341(2) . ?
O2 C12 1.477(2) . ?
O3 C12 1.387(2) . ?
O3 H3A 0.94(2) . ?
C1 C2 1.380(2) . ?
C1 C10 1.419(2) . ?
C1 C11 1.480(2) . ?
C2 C3 1.414(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.370(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.419(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.418(2) . ?
C5 C10 1.426(2) . ?
C6 C7 1.373(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.417(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.374(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.419(2) . ?
C9 C12 1.508(2) . ?
C12 H12 1.0000 . ?

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 O2 C12 125.76(10) . . ?
C12 O3 H3A 107.6(12) . . ?
C2 C1 C10 121.41(12) . . ?
C2 C1 C11 119.63(14) . . ?
C10 C1 C11 118.89(13) . . ?
C1 C2 C3 119.62(15) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 H2 120.2 . . ?
C4 C3 C2 120.18(15) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C5 121.53(13) . . ?
C3 C4 H4 119.2 . . ?
C5 C4 H4 119.2 . . ?
C6 C5 C4 123.08(13) . . ?
C6 C5 C10 118.34(14) . . ?
C4 C5 C10 118.57(14) . . ?
C7 C6 C5 120.93(13) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C6 C7 C8 120.45(15) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 H7 119.8 . . ?
C9 C8 C7 120.18(14) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C8 C9 C10 120.28(13) . . ?
C8 C9 C12 119.43(14) . . ?
C10 C9 C12 120.16(13) . . ?
C9 C10 C1 121.59(12) . . ?
C9 C10 C5 119.77(14) . . ?
C1 C10 C5 118.63(14) . . ?
O1 C11 O2 117.49(12) . . ?
O1 C11 C1 123.46(13) . . ?
O2 C11 C1 119.01(13) . . ?
O3 C12 O2 106.67(12) . . ?
O3 C12 C9 110.90(14) . . ?
O2 C12 C9 113.14(12) . . ?
O3 C12 H12 108.7 . . ?
O2 C12 H12 108.7 . . ?
C9 C12 H12 108.7 . . ?

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
O3 H3A O1 0.94(2) 1.84(2) 2.785(3) 176.6(18) 2
C12 H12 O2 1.00 2.54 3.183(3) 122.1 2

_refine_diff_density_max         0.242
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.054

_shelxl_version_number           2013-4

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetonitrile'
####################################################################### 
# 
# 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_lithiumtwin
_database_code_depnum_ccdc_archive 'CCDC 1435390'
_audit_update_record             
;
2015-11-05 deposited with the CCDC.
2016-01-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
lithium naphthalaldehydate  Li.14
;
_chemical_name_common            ?
_chemical_melting_point          600-602
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H7 Li O3'
_chemical_formula_weight         206.12

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'
Li Li -0.0003 0.0001 '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/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                   14.953(2)
_cell_length_b                   5.0185(6)
_cell_length_c                   12.3691(19)
_cell_angle_alpha                90
_cell_angle_beta                 100.389(13)
_cell_angle_gamma                90
_cell_volume                     913.0(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    151(2)
_cell_measurement_reflns_used    1258
_cell_measurement_theta_min      3.3423
_cell_measurement_theta_max      28.7126

_exptl_crystal_description       plate
_exptl_crystal_colour            beige
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.499
_exptl_crystal_F_000             424
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.4360
_exptl_crystal_size_mid          0.2198
_exptl_crystal_size_min          0.0871
_exptl_absorpt_coefficient_mu    0.106
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.967
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_special_details           
;
Refined as twin with 1 0 0.44  0 -1 0 0 0 -1 twin matrix 
(2-fold axis rotation about [1 00] reciprocal lattice direction). 
;

_diffrn_ambient_temperature      151(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_detector_area_resol_mean 15.9832
_diffrn_reflns_number            1601
_diffrn_reflns_av_unetI/netI     0.0656
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.349
_diffrn_reflns_theta_max         25.022
_diffrn_reflns_theta_full        25.250
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.979
_reflns_number_total             1601
_reflns_number_gt                1438
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39) 
;
_computing_structure_solution    SHELXS
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          Twin
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1261P)²+19.8887P] 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         1601
_refine_ls_number_parameters     146
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1705
_refine_ls_R_factor_gt           0.1629
_refine_ls_wR_factor_ref         0.4719
_refine_ls_wR_factor_gt          0.4689
_refine_ls_goodness_of_fit_ref   1.193
_refine_ls_restrained_S_all      1.193
_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_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 0.5589(5) 0.6918(16) 1.2089(7) 0.0202(19) Uani 1 1 d . . . . .
O2 O 0.5918(5) 0.2861(15) 1.1544(7) 0.023(2) Uani 1 1 d . . . . .
O3 O 0.6013(5) 0.0322(17) 0.9335(7) 0.024(2) Uani 1 1 d . . . . .
C1 C 0.7051(8) 0.616(2) 1.1654(9) 0.019(3) Uani 1 1 d . . . . .
C2 C 0.7422(8) 0.821(2) 1.2339(9) 0.019(3) Uani 1 1 d . . . . .
H2 H 0.7042 0.9240 1.2716 0.023 Uiso 1 1 calc R U . . .
C3 C 0.8357(8) 0.878(3) 1.2486(10) 0.025(3) Uani 1 1 d . . . . .
H3 H 0.8599 1.0223 1.2946 0.029 Uiso 1 1 calc R U . . .
C4 C 0.8924(8) 0.728(3) 1.1969(10) 0.027(3) Uani 1 1 d . . . . .
H4 H 0.9562 0.7588 1.2116 0.032 Uiso 1 1 calc R U . . .
C5 C 0.8551(8) 0.528(3) 1.1218(10) 0.023(3) Uani 1 1 d . . . . .
C6 C 0.9135(8) 0.376(3) 1.0688(11) 0.025(3) Uani 1 1 d . . . . .
H6 H 0.9770 0.4106 1.0847 0.030 Uiso 1 1 calc R U . . .
C7 C 0.8821(8) 0.183(3) 0.9962(10) 0.026(3) Uani 1 1 d . . . . .
H7 H 0.9230 0.0813 0.9625 0.032 Uiso 1 1 calc R U . . .
C8 C 0.7884(8) 0.135(3) 0.9707(9) 0.022(3) Uani 1 1 d . . . . .
H8 H 0.7657 0.0017 0.9184 0.027 Uiso 1 1 calc R U . . .
C9 C 0.7290(8) 0.279(2) 1.0206(9) 0.020(3) Uani 1 1 d . . . . .
C10 C 0.7600(7) 0.474(2) 1.1016(8) 0.017(2) Uani 1 1 d . . . . .
C11 C 0.6102(7) 0.529(2) 1.1738(9) 0.017(2) Uani 1 1 d . . . . .
C12 C 0.6320(7) 0.244(2) 0.9721(10) 0.021(3) Uani 1 1 d . . . . .
H12 H 0.5920 0.3915 0.9710 0.025 Uiso 1 1 calc R U . . .
Li1 Li 0.4950(15) -0.036(4) 0.8200(15) 0.024(4) 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
O1 C11 1.253(13) . ?
O1 Li1 1.91(2) 3_667 ?
O1 Li1 1.97(2) 4_566 ?
O2 C11 1.261(14) . ?
O2 Li1 1.87(2) 3_657 ?
O3 C12 1.220(15) . ?
O3 Li1 1.95(2) . ?
C1 C2 1.383(17) . ?
C1 C10 1.430(16) . ?
C1 C11 1.506(16) . ?
C2 C3 1.407(17) . ?
C3 C4 1.376(18) . ?
C4 C5 1.415(18) . ?
C5 C6 1.407(18) . ?
C5 C10 1.425(15) . ?
C6 C7 1.345(18) . ?
C7 C8 1.401(17) . ?
C8 C9 1.373(17) . ?
C9 C10 1.418(16) . ?
C9 C12 1.477(15) . ?
C11 Li1 2.71(2) 4_566 ?
Li1 O2 1.87(2) 3_657 ?
Li1 O1 1.91(2) 3_667 ?
Li1 O1 1.97(2) 4_565 ?
Li1 C11 2.71(2) 4_565 ?
Li1 Li1 3.07(2) 2_646 ?
Li1 Li1 3.07(2) 2_656 ?

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 O1 Li1 142.2(10) . 3_667 ?
C11 O1 Li1 112.7(9) . 4_566 ?
Li1 O1 Li1 104.4(6) 3_667 4_566 ?
C11 O2 Li1 138.5(10) . 3_657 ?
C12 O3 Li1 129.4(10) . . ?
C2 C1 C10 120.2(10) . . ?
C2 C1 C11 117.0(10) . . ?
C10 C1 C11 122.2(10) . . ?
C1 C2 C3 120.7(11) . . ?
C4 C3 C2 120.7(12) . . ?
C3 C4 C5 119.5(11) . . ?
C6 C5 C4 119.1(11) . . ?
C6 C5 C10 120.0(12) . . ?
C4 C5 C10 120.9(11) . . ?
C7 C6 C5 121.9(11) . . ?
C6 C7 C8 119.3(11) . . ?
C9 C8 C7 120.7(11) . . ?
C8 C9 C10 121.6(11) . . ?
C8 C9 C12 115.0(11) . . ?
C10 C9 C12 122.7(11) . . ?
C9 C10 C5 116.4(10) . . ?
C9 C10 C1 126.0(10) . . ?
C5 C10 C1 117.6(10) . . ?
O1 C11 O2 124.8(11) . . ?
O1 C11 C1 118.4(10) . . ?
O2 C11 C1 116.4(10) . . ?
O1 C11 Li1 42.1(7) . 4_566 ?
O2 C11 Li1 89.8(9) . 4_566 ?
C1 C11 Li1 139.5(9) . 4_566 ?
O3 C12 C9 122.3(11) . . ?
O2 Li1 O1 110.8(11) 3_657 3_667 ?
O2 Li1 O3 119.7(11) 3_657 . ?
O1 Li1 O3 103.7(10) 3_667 . ?
O2 Li1 O1 106.8(10) 3_657 4_565 ?
O1 Li1 O1 118.0(10) 3_667 4_565 ?
O3 Li1 O1 97.9(10) . 4_565 ?
O2 Li1 C11 131.6(10) 3_657 4_565 ?
O1 Li1 C11 99.2(9) 3_667 4_565 ?
O3 Li1 C11 86.8(8) . 4_565 ?
O1 Li1 C11 25.2(4) 4_565 4_565 ?
O2 Li1 Li1 69.7(6) 3_657 2_646 ?
O1 Li1 Li1 134.0(12) 3_667 2_646 ?
O3 Li1 Li1 115.7(12) . 2_646 ?
O1 Li1 Li1 37.1(7) 4_565 2_646 ?
C11 Li1 Li1 62.2(8) 4_565 2_646 ?
O2 Li1 Li1 138.5(14) 3_657 2_656 ?
O1 Li1 Li1 38.5(3) 3_667 2_656 ?
O3 Li1 Li1 98.4(9) . 2_656 ?
O1 Li1 Li1 81.5(10) 4_565 2_656 ?
C11 Li1 Li1 60.7(8) 4_565 2_656 ?
Li1 Li1 Li1 109.8(11) 2_646 2_656 ?

_refine_diff_density_max         0.865
_refine_diff_density_min         -0.951
_refine_diff_density_rms         0.210

_vrf_RFACR01_lithiumtwin         
; 
PROBLEM: the value of the weighted R factor is > 0.45
            Weighted R factor given   0.472   

RESPONSE: The structure is refined as a twin using
with 1 0 0.44  0 -1 0 0 0 -1 twin matrix (2-fold axis rotation
about [1 00] reciprocal lattice direction).
This is the best result obtained, even though several
crystals were studied. The R (F>2sigmaF) is 16%.
;


_shelxl_version_number           2013-4

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol/water'
####################################################################### 
# 
# 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_KINVTC
_database_code_depnum_ccdc_archive 'CCDC 1435391'
_audit_update_record             
;
2015-11-05 deposited with the CCDC.
2016-01-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
naphthaldic acid potassium salt .1H2O K.14.H2O
;
_chemical_name_common            ?
_chemical_melting_point          563
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H9 K O4'
_chemical_formula_weight         256.29

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
K K 0.2009 0.2494 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

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

_cell_length_a                   7.3837(4)
_cell_length_b                   30.138(2)
_cell_length_c                   4.8965(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1089.61(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    1444
_cell_measurement_theta_min      3.4220
_cell_measurement_theta_max      28.1230

_exptl_crystal_description       'thin needle'
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.3689
_exptl_crystal_size_mid          0.0986
_exptl_crystal_size_min          0.0927
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.562
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             528
_exptl_absorpt_coefficient_mu    0.486
_exptl_absorpt_correction_T_min  0.903
_exptl_absorpt_correction_T_max  0.961
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_special_details           
;
 ?
;
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini'
_diffrn_detector_area_resol_mean 15.9832
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_number            3448
_diffrn_reflns_av_unetI/netI     0.0632
_diffrn_reflns_av_R_equivalents  0.0536
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       4
_diffrn_reflns_theta_min         3.072
_diffrn_reflns_theta_max         28.839
_diffrn_reflns_theta_full        27.000
_diffrn_measured_fraction_theta_max 0.891
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.891
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.650
_diffrn_reflns_point_group_measured_fraction_full 0.731
_reflns_number_total             1852
_reflns_number_gt                1674
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.311
_reflns_Friedel_fraction_max     0.347
_reflns_Friedel_fraction_full    0.404

_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_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)+(0.0424P)²+6.6604P] 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_abs_structure_details 
;
 Flack x determined using 360 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.09(11)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1852
_refine_ls_number_parameters     154
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0858
_refine_ls_R_factor_gt           0.0782
_refine_ls_wR_factor_ref         0.1848
_refine_ls_wR_factor_gt          0.1806
_refine_ls_goodness_of_fit_ref   1.122
_refine_ls_restrained_S_all      1.122
_refine_ls_shift/su_max          0.008
_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
K1 K 0.1070(2) 0.71925(5) 0.6626(4) 0.0226(4) Uani 1 1 d . . . . .
O1 O 0.2602(8) 0.8116(2) 0.8484(15) 0.0299(15) Uani 1 1 d . . . . .
O2 O -0.0409(8) 0.80252(17) 0.8340(14) 0.0238(13) Uani 1 1 d . . . . .
O3 O -0.3432(8) 0.8400(2) 1.2346(14) 0.0332(16) Uani 1 1 d . . . . .
O4 O -0.1461(8) 0.74442(19) 0.2777(13) 0.0283(14) Uani 1 1 d . . . . .
H41 H -0.1090 0.7650 0.1780 0.034 Uiso 1 1 d . U . . .
H42 H -0.1770 0.7240 0.1650 0.034 Uiso 1 1 d . U . . .
C1 C 0.0811(9) 0.8714(2) 0.680(2) 0.0180(15) Uani 1 1 d . . . . .
C2 C 0.2147(11) 0.8854(3) 0.512(2) 0.027(2) Uani 1 1 d . . . . .
H2 H 0.3227 0.8684 0.4986 0.032 Uiso 1 1 calc R U . . .
C3 C 0.1981(12) 0.9242(3) 0.358(3) 0.038(3) Uani 1 1 d . . . . .
H3 H 0.2965 0.9339 0.2480 0.045 Uiso 1 1 calc R U . . .
C4 C 0.0424(12) 0.9483(3) 0.364(2) 0.027(2) Uani 1 1 d . . . . .
H4 H 0.0297 0.9737 0.2507 0.033 Uiso 1 1 calc R U . . .
C5 C -0.0996(11) 0.9355(2) 0.538(2) 0.0227(18) Uani 1 1 d . . . . .
C6 C -0.2658(12) 0.9599(3) 0.538(2) 0.027(2) Uani 1 1 d . . . . .
H6 H -0.2781 0.9852 0.4236 0.032 Uiso 1 1 calc R U . . .
C7 C -0.4063(10) 0.9474(3) 0.700(2) 0.032(2) Uani 1 1 d . . . . .
H7 H -0.5180 0.9630 0.6928 0.038 Uiso 1 1 calc R U . . .
C8 C -0.3854(12) 0.9113(3) 0.878(2) 0.029(2) Uani 1 1 d . . . . .
H8 H -0.4839 0.9031 0.9921 0.035 Uiso 1 1 calc R U . . .
C9 C -0.2270(10) 0.8875(2) 0.8927(17) 0.0173(17) Uani 1 1 d . . . . .
C10 C -0.0797(9) 0.8980(2) 0.7084(16) 0.0153(16) Uani 1 1 d . . . . .
C11 C 0.1043(11) 0.8252(3) 0.8046(18) 0.0206(17) Uani 1 1 d . . . . .
C12 C -0.2129(11) 0.8570(2) 1.1266(19) 0.0225(18) Uani 1 1 d . . . . .
H12 H -0.0959 0.8504 1.1964 0.027 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
K1 O4 2.760(7) . ?
K1 O3 2.778(7) 4_564 ?
K1 O2 2.810(6) 4_565 ?
K1 O4 2.842(7) 4_565 ?
K1 O2 2.863(6) . ?
K1 O1 2.872(6) 4_465 ?
K1 O1 3.140(7) . ?
K1 C11 3.268(8) . ?
K1 O3 3.341(7) 4_565 ?
K1 C12 3.495(9) 4_565 ?
K1 K1 4.1309(14) 4_565 ?
K1 K1 4.1309(14) 4_465 ?
O1 C11 1.241(10) . ?
O1 K1 2.872(6) 4_565 ?
O2 C11 1.280(9) . ?
O2 K1 2.810(6) 4_465 ?
O3 C12 1.212(10) . ?
O3 K1 2.778(7) 4_466 ?
O3 K1 3.341(7) 4_465 ?
O4 K1 2.842(6) 4_465 ?
C1 C2 1.352(11) . ?
C1 C10 1.440(9) . ?
C1 C11 1.528(11) . ?
C2 C3 1.400(12) . ?
C3 C4 1.359(12) . ?
C4 C5 1.405(12) . ?
C5 C10 1.413(11) . ?
C5 C6 1.431(11) . ?
C6 C7 1.360(12) . ?
C7 C8 1.401(13) . ?
C8 C9 1.375(11) . ?
C9 C10 1.448(11) . ?
C9 C12 1.471(12) . ?
C12 K1 3.495(9) 4_465 ?

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
O4 K1 O3 75.58(19) . 4_564 ?
O4 K1 O2 153.4(2) . 4_565 ?
O3 K1 O2 87.29(18) 4_564 4_565 ?
O4 K1 O4 82.85(17) . 4_565 ?
O3 K1 O4 70.25(18) 4_564 4_565 ?
O2 K1 O4 72.20(18) 4_565 4_565 ?
O4 K1 O2 72.61(19) . . ?
O3 K1 O2 146.6(2) 4_564 . ?
O2 K1 O2 118.0(2) 4_565 . ?
O4 K1 O2 95.83(17) 4_565 . ?
O4 K1 O1 72.7(2) . 4_465 ?
O3 K1 O1 98.56(19) 4_564 4_465 ?
O2 K1 O1 130.88(19) 4_565 4_465 ?
O4 K1 O1 155.1(2) 4_565 4_465 ?
O2 K1 O1 81.44(17) . 4_465 ?
O4 K1 O1 101.42(17) . . ?
O3 K1 O1 137.80(19) 4_564 . ?
O2 K1 O1 77.71(16) 4_565 . ?
O4 K1 O1 67.63(18) 4_565 . ?
O2 K1 O1 43.54(15) . . ?
O1 K1 O1 121.1(2) 4_465 . ?
O4 K1 C11 82.7(2) . . ?
O3 K1 C11 142.1(2) 4_564 . ?
O2 K1 C11 99.81(19) 4_565 . ?
O4 K1 C11 76.62(19) 4_565 . ?
O2 K1 C11 22.89(17) . . ?
O1 K1 C11 104.12(19) 4_465 . ?
O1 K1 C11 22.21(17) . . ?
O4 K1 O3 142.53(17) . 4_565 ?
O3 K1 O3 105.93(19) 4_564 4_565 ?
O2 K1 O3 61.51(16) 4_565 4_565 ?
O4 K1 O3 133.71(17) 4_565 4_565 ?
O2 K1 O3 105.35(18) . 4_565 ?
O1 K1 O3 70.09(18) 4_465 4_565 ?
O1 K1 O3 101.02(18) . 4_565 ?
C11 K1 O3 110.2(2) . 4_565 ?
O4 K1 C12 151.91(19) . 4_565 ?
O3 K1 C12 91.0(2) 4_564 4_565 ?
O2 K1 C12 45.58(18) 4_565 4_565 ?
O4 K1 C12 116.12(19) 4_565 4_565 ?
O2 K1 C12 122.1(2) . 4_565 ?
O1 K1 C12 85.4(2) 4_465 4_565 ?
O1 K1 C12 104.94(19) . 4_565 ?
C11 K1 C12 120.5(2) . 4_565 ?
O3 K1 C12 20.26(16) 4_565 4_565 ?
O4 K1 K1 118.79(13) . 4_565 ?
O3 K1 K1 99.79(13) 4_564 4_565 ?
O2 K1 K1 43.77(11) 4_565 4_565 ?
O4 K1 K1 41.73(14) 4_565 4_565 ?
O2 K1 K1 87.00(13) . 4_565 ?
O1 K1 K1 160.40(14) 4_465 4_565 ?
O1 K1 K1 43.96(11) . 4_565 ?
C11 K1 K1 64.35(15) . 4_565 ?
O3 K1 K1 98.12(11) 4_565 4_565 ?
C12 K1 K1 87.42(13) 4_565 4_565 ?
O4 K1 K1 43.26(14) . 4_465 ?
O3 K1 K1 114.00(13) 4_564 4_465 ?
O2 K1 K1 158.71(14) 4_565 4_465 ?
O4 K1 K1 113.62(13) 4_565 4_465 ?
O2 K1 K1 42.76(13) . 4_465 ?
O1 K1 K1 49.36(13) 4_465 4_465 ?
O1 K1 K1 85.65(12) . 4_465 ?
C11 K1 K1 63.65(15) . 4_465 ?
O3 K1 K1 109.76(10) 4_565 4_465 ?
C12 K1 K1 129.44(14) 4_565 4_465 ?
K1 K1 K1 126.69(8) 4_565 4_465 ?
C11 O1 K1 151.6(6) . 4_565 ?
C11 O1 K1 84.7(5) . . ?
K1 O1 K1 86.67(17) 4_565 . ?
C11 O2 K1 150.0(6) . 4_465 ?
C11 O2 K1 96.6(5) . . ?
K1 O2 K1 93.47(17) 4_465 . ?
C12 O3 K1 135.0(6) . 4_466 ?
C12 O3 K1 87.0(5) . 4_465 ?
K1 O3 K1 105.93(19) 4_466 4_465 ?
K1 O4 K1 95.0(2) . 4_465 ?
C2 C1 C10 119.1(7) . . ?
C2 C1 C11 116.4(6) . . ?
C10 C1 C11 124.1(6) . . ?
C1 C2 C3 121.7(8) . . ?
C4 C3 C2 120.6(9) . . ?
C3 C4 C5 119.8(8) . . ?
C4 C5 C10 120.0(7) . . ?
C4 C5 C6 119.9(8) . . ?
C10 C5 C6 120.0(8) . . ?
C7 C6 C5 120.8(8) . . ?
C6 C7 C8 119.6(7) . . ?
C9 C8 C7 122.1(8) . . ?
C8 C9 C10 119.5(7) . . ?
C8 C9 C12 115.3(7) . . ?
C10 C9 C12 124.6(7) . . ?
C5 C10 C1 118.4(7) . . ?
C5 C10 C9 117.7(6) . . ?
C1 C10 C9 123.9(7) . . ?
O1 C11 O2 125.6(7) . . ?
O1 C11 C1 118.2(7) . . ?
O2 C11 C1 116.0(7) . . ?
O1 C11 K1 73.1(5) . . ?
O2 C11 K1 60.5(4) . . ?
C1 C11 K1 143.7(6) . . ?
O3 C12 C9 123.2(8) . . ?
O3 C12 K1 72.7(5) . 4_465 ?
C9 C12 K1 83.0(5) . 4_465 ?

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
O4 H41 O2 0.835(6) 2.090(6) 2.896(9) 162.1(5) 1_554
O4 H42 O1 0.858(6) 1.942(7) 2.784(9) 166.9(5) 4_464

_refine_diff_density_max         1.055
_refine_diff_density_min         -1.213
_refine_diff_density_rms         0.124

_shelxl_version_number           2013-4

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: isopropanol'
####################################################################### 
# 
# 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_CSSALT
_database_code_depnum_ccdc_archive 'CCDC 1435392'
_audit_update_record             
;
2015-11-05 deposited with the CCDC.
2016-01-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
naphthalaldehydic acid cesium salt. 1H2O Cs.14.H2O
;
_chemical_name_common            ?
_chemical_melting_point          545-548
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H9 Cs O4'
_chemical_formula_weight         350.10

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cs Cs -0.3680 2.1192 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

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

_cell_length_a                   7.852(6)
_cell_length_b                   29.89(2)
_cell_length_c                   4.998(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1173.0(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2647
_cell_measurement_theta_min      2.6
_cell_measurement_theta_max      27.6

_exptl_crystal_description       needle
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.982
_exptl_crystal_F_000             672
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_absorpt_coefficient_mu    3.156
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.657
_exptl_absorpt_process_details   
;
CrystalClear-SM Expert 2.0 r11 (Rigaku, 2011)
;
_exptl_special_details           
;
 ?
;
_diffrn_ambient_temperature      100
_diffrn_source_power             2.5
_diffrn_source_voltage           45.0
_diffrn_source_current           55.0
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           'Mo K\a'
_diffrn_source                   'Rotating Anode'
_diffrn_radiation_monochromator  Confocal
_diffrn_measurement_specimen_support Mitegen
_diffrn_detector                 CCD
_diffrn_measurement_device       
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type  
;
Rigaku Saturn724+ (2x2 bin mode)
;
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_reflns_number            6320
_diffrn_reflns_av_unetI/netI     0.0809
_diffrn_reflns_av_R_equivalents  0.0573
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         2.682
_diffrn_reflns_theta_max         27.610
_diffrn_reflns_theta_full        27.000
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measured_fraction_theta_full 0.969
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_Laue_measured_fraction_full 0.969
_diffrn_reflns_point_group_measured_fraction_max 0.856
_diffrn_reflns_point_group_measured_fraction_full 0.870
_reflns_number_total             2337
_reflns_number_gt                1979
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.606
_reflns_Friedel_fraction_max     0.730
_reflns_Friedel_fraction_full    0.746

_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       
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_structure_solution    'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_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)+(0.0386P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 594 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.05(3)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2337
_refine_ls_number_parameters     161
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.0586
_refine_ls_R_factor_gt           0.0478
_refine_ls_wR_factor_ref         0.0994
_refine_ls_wR_factor_gt          0.0930
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.048
_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
Cs1 Cs 0.45391(7) 0.28719(2) 0.7705(3) 0.01752(18) Uani 1 1 d . . . . .
O1 O 0.3100(10) 0.1858(3) 0.9742(16) 0.0273(19) Uani 1 1 d . . . . .
O2 O 0.5929(10) 0.1901(2) 0.9520(15) 0.0206(18) Uani 1 1 d . . . . .
O3 O 0.8823(9) 0.1461(2) 1.300(3) 0.026(2) Uani 1 1 d . . . . .
O4 O 0.7040(10) 0.2522(2) 0.3460(13) 0.021(2) Uani 1 1 d D . . . .
H41 H 0.749(11) 0.2720(19) 0.246(12) 0.02(3) Uiso 1 1 d D . . . .
H42 H 0.672(13) 0.232(2) 0.237(12) 0.030 Uiso 1 1 d D U . . .
C1 C 0.4602(11) 0.1250(3) 0.789(6) 0.015(2) Uani 1 1 d . U . . .
C2 C 0.3256(15) 0.1131(3) 0.631(2) 0.023(2) Uani 1 1 d . U . . .
H2 H 0.2261 0.1312 0.6393 0.027 Uiso 1 1 calc R U . . .
C3 C 0.3241(15) 0.0758(4) 0.456(2) 0.024(3) Uani 1 1 d . . . . .
H3 H 0.2269 0.0692 0.3505 0.029 Uiso 1 1 calc R U . . .
C4 C 0.4671(15) 0.0498(3) 0.445(2) 0.022(3) Uani 1 1 d . . . . .
H4 H 0.4698 0.0249 0.3273 0.026 Uiso 1 1 calc R U . . .
C5 C 0.6113(15) 0.0592(3) 0.607(2) 0.018(2) Uani 1 1 d . U . . .
C6 C 0.7609(15) 0.0330(3) 0.581(2) 0.023(3) Uani 1 1 d . . . . .
H6 H 0.7623 0.0084 0.4607 0.027 Uiso 1 1 calc R U . . .
C7 C 0.9035(14) 0.0428(3) 0.727(4) 0.029(4) Uani 1 1 d . . . . .
H7 H 1.0055 0.0264 0.6991 0.035 Uiso 1 1 calc R U . . .
C8 C 0.8986(15) 0.0764(4) 0.914(2) 0.023(3) Uani 1 1 d . . . . .
H8 H 0.9975 0.0824 1.0178 0.027 Uiso 1 1 calc R U . . .
C9 C 0.7533(15) 0.1018(3) 0.956(2) 0.019(2) Uani 1 1 d . . . . .
C10 C 0.6073(12) 0.0958(3) 0.790(4) 0.016(2) Uani 1 1 d . U . . .
C11 C 0.4523(14) 0.1699(3) 0.918(2) 0.016(2) Uani 1 1 d . U . . .
C12 C 0.7531(15) 0.1309(3) 1.201(2) 0.021(3) Uani 1 1 d . . . . .
H12 H 0.6470 0.1379 1.2824 0.025 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
Cs1 O2 3.052(8) 4_455 ?
Cs1 O4 3.074(8) . ?
Cs1 O1 3.083(8) 4 ?
Cs1 O4 3.121(8) 4_455 ?
Cs1 O3 3.135(11) 4_454 ?
Cs1 O2 3.231(8) . ?
Cs1 O3 3.359(12) 4_455 ?
Cs1 O1 3.391(8) . ?
Cs1 C11 3.584(10) . ?
Cs1 C12 3.619(10) 4_455 ?
Cs1 O4 3.636(8) 1_556 ?
Cs1 O4 3.675(8) 4_456 ?
O1 C11 1.248(12) . ?
O1 Cs1 3.083(8) 4_455 ?
O2 C11 1.270(13) . ?
O2 Cs1 3.052(8) 4 ?
O3 C12 1.216(13) . ?
O3 Cs1 3.135(11) 4_556 ?
O3 Cs1 3.359(12) 4 ?
O4 Cs1 3.121(8) 4 ?
O4 Cs1 3.636(8) 1_554 ?
O4 Cs1 3.675(8) 4_554 ?
C1 C2 1.36(2) . ?
C1 C10 1.449(11) . ?
C1 C11 1.490(18) . ?
C2 C3 1.417(13) . ?
C3 C4 1.368(15) . ?
C4 C5 1.418(16) . ?
C5 C6 1.417(15) . ?
C5 C10 1.426(17) . ?
C6 C7 1.368(16) . ?
C7 C8 1.374(18) . ?
C8 C9 1.386(15) . ?
C9 C10 1.427(18) . ?
C9 C12 1.501(15) . ?
C9 Cs1 3.789(10) 4 ?
C12 Cs1 3.619(10) 4 ?

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
O2 Cs1 O4 150.9(2) 4_455 . ?
O2 Cs1 O1 133.3(2) 4_455 4 ?
O4 Cs1 O1 74.8(2) . 4 ?
O2 Cs1 O4 72.7(2) 4_455 4_455 ?
O4 Cs1 O4 78.70(16) . 4_455 ?
O1 Cs1 O4 153.3(2) 4 4_455 ?
O2 Cs1 O3 85.1(2) 4_455 4_454 ?
O4 Cs1 O3 79.2(2) . 4_454 ?
O1 Cs1 O3 104.1(2) 4 4_454 ?
O4 Cs1 O3 67.5(2) 4_455 4_454 ?
O2 Cs1 O2 115.5(2) 4_455 . ?
O4 Cs1 O2 70.87(19) . . ?
O1 Cs1 O2 80.6(2) 4 . ?
O4 Cs1 O2 93.69(18) 4_455 . ?
O3 Cs1 O2 147.4(2) 4_454 . ?
O2 Cs1 O3 58.58(19) 4_455 4_455 ?
O4 Cs1 O3 148.44(18) . 4_455 ?
O1 Cs1 O3 74.7(2) 4 4_455 ?
O4 Cs1 O3 130.84(18) 4_455 4_455 ?
O3 Cs1 O3 100.58(18) 4_454 4_455 ?
O2 Cs1 O3 111.6(2) . 4_455 ?
O2 Cs1 O1 78.46(19) 4_455 . ?
O4 Cs1 O1 96.66(18) . . ?
O1 Cs1 O1 115.9(2) 4 . ?
O4 Cs1 O1 69.96(19) 4_455 . ?
O3 Cs1 O1 137.2(2) 4_454 . ?
O2 Cs1 O1 39.23(19) . . ?
O3 Cs1 O1 103.8(2) 4_455 . ?
O2 Cs1 C11 98.8(2) 4_455 . ?
O4 Cs1 C11 79.1(2) . . ?
O1 Cs1 C11 101.0(2) 4 . ?
O4 Cs1 C11 76.6(2) 4_455 . ?
O3 Cs1 C11 140.9(2) 4_454 . ?
O2 Cs1 C11 20.7(2) . . ?
O3 Cs1 C11 114.7(2) 4_455 . ?
O1 Cs1 C11 20.4(2) . . ?
O2 Cs1 C12 43.0(2) 4_455 4_455 ?
O4 Cs1 C12 156.7(2) . 4_455 ?
O1 Cs1 C12 91.3(2) 4 4_455 ?
O4 Cs1 C12 112.7(2) 4_455 4_455 ?
O3 Cs1 C12 86.5(3) 4_454 4_455 ?
O2 Cs1 C12 126.0(2) . 4_455 ?
O3 Cs1 C12 19.6(2) 4_455 4_455 ?
O1 Cs1 C12 106.3(2) . 4_455 ?
C11 Cs1 C12 122.6(2) . 4_455 ?
O2 Cs1 O4 109.3(2) 4_455 1_556 ?
O4 Cs1 O4 95.9(2) . 1_556 ?
O1 Cs1 O4 47.50(18) 4 1_556 ?
O4 Cs1 O4 140.24(6) 4_455 1_556 ?
O3 Cs1 O4 150.87(18) 4_454 1_556 ?
O2 Cs1 O4 48.47(17) . 1_556 ?
O3 Cs1 O4 68.80(19) 4_455 1_556 ?
O1 Cs1 O4 71.66(18) . 1_556 ?
C11 Cs1 O4 63.7(2) . 1_556 ?
C12 Cs1 O4 87.7(2) 4_455 1_556 ?
O2 Cs1 O4 48.92(18) 4_455 4_456 ?
O4 Cs1 O4 140.53(6) . 4_456 ?
O1 Cs1 O4 108.0(2) 4 4_456 ?
O4 Cs1 O4 94.3(2) 4_455 4_456 ?
O3 Cs1 O4 134.1(2) 4_454 4_456 ?
O2 Cs1 O4 70.90(18) . 4_456 ?
O3 Cs1 O4 59.0(2) 4_455 4_456 ?
O1 Cs1 O4 45.64(17) . 4_456 ?
C11 Cs1 O4 61.6(2) . 4_456 ?
C12 Cs1 O4 61.3(2) 4_455 4_456 ?
O4 Cs1 O4 64.99(12) 1_556 4_456 ?
C11 O1 Cs1 147.0(7) . 4_455 ?
C11 O1 Cs1 88.6(6) . . ?
Cs1 O1 Cs1 88.2(2) 4_455 . ?
C11 O2 Cs1 150.8(7) . 4 ?
C11 O2 Cs1 95.6(6) . . ?
Cs1 O2 Cs1 91.8(2) 4 . ?
C12 O3 Cs1 133.7(8) . 4_556 ?
C12 O3 Cs1 92.4(8) . 4 ?
Cs1 O3 Cs1 100.58(18) 4_556 4 ?
Cs1 O4 Cs1 93.5(2) . 4 ?
Cs1 O4 Cs1 95.9(2) . 1_554 ?
Cs1 O4 Cs1 170.4(3) 4 1_554 ?
Cs1 O4 Cs1 171.9(3) . 4_554 ?
Cs1 O4 Cs1 94.3(2) 4 4_554 ?
Cs1 O4 Cs1 76.21(15) 1_554 4_554 ?
C2 C1 C10 117.6(15) . . ?
C2 C1 C11 116.9(9) . . ?
C10 C1 C11 125.0(13) . . ?
C1 C2 C3 124.5(11) . . ?
C4 C3 C2 117.8(11) . . ?
C3 C4 C5 121.3(10) . . ?
C6 C5 C4 120.0(10) . . ?
C6 C5 C10 119.9(11) . . ?
C4 C5 C10 120.0(10) . . ?
C7 C6 C5 120.8(11) . . ?
C6 C7 C8 119.8(10) . . ?
C7 C8 C9 121.8(11) . . ?
C8 C9 C10 120.2(11) . . ?
C8 C9 C12 116.2(10) . . ?
C10 C9 C12 123.2(10) . . ?
C8 C9 Cs1 95.7(7) . 4 ?
C10 C9 Cs1 107.6(7) . 4 ?
C12 C9 Cs1 72.0(5) . 4 ?
C5 C10 C9 117.0(9) . . ?
C5 C10 C1 118.5(14) . . ?
C9 C10 C1 124.5(14) . . ?
O1 C11 O2 124.5(10) . . ?
O1 C11 C1 118.6(10) . . ?
O2 C11 C1 116.8(9) . . ?
O1 C11 Cs1 71.0(6) . . ?
O2 C11 Cs1 63.8(5) . . ?
C1 C11 Cs1 142.4(12) . . ?
O3 C12 C9 123.1(11) . . ?
O3 C12 Cs1 68.0(7) . 4 ?
C9 C12 Cs1 84.7(6) . 4 ?

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
O4 H41 O1 0.850(7) 1.92(2) 2.753(10) 168(9) 4_554
O4 H42 O2 0.850(7) 1.997(16) 2.843(10) 173(8) 1_554

_refine_diff_density_max         2.602
_refine_diff_density_min         -1.268
_refine_diff_density_rms         0.178

_shelxl_version_number           2013-4

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethanol/water'
####################################################################### 
# 
# 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_PhNH3Csalt
_database_code_depnum_ccdc_archive 'CCDC 1435393'
_audit_update_record             
;
2015-11-05 deposited with the CCDC.
2016-01-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
"N,N',N''-triphenylguanidinium naphthalaldehydate,(PhNH)3C.15"
_chemical_name_common            ?
_chemical_melting_point          402-404
_chemical_formula_moiety         ?
_chemical_formula_sum            'C31 H25 N3 O3'
_chemical_formula_weight         487.54

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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

_cell_length_a                   20.9749(14)
_cell_length_b                   19.1882(6)
_cell_length_c                   13.2738(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5342.3(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    26863
_cell_measurement_theta_min      3.1
_cell_measurement_theta_max      27.5

_exptl_crystal_description       Plate
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.212
_exptl_crystal_F_000             2048
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.430
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.079
_shelx_estimated_absorpt_T_min   0.967
_shelx_estimated_absorpt_T_max   0.998
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.733

_exptl_absorpt_process_details   
;
 CrystalClear-SM Expert 3.1 b27 (Rigaku, 2012)
;
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_source_power             2.5
_diffrn_source_voltage           45.0
_diffrn_source_current           55.0
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           'Mo K\a'
_diffrn_source                   'Rotating Anode'
_diffrn_radiation_monochromator  Confocal
_diffrn_measurement_specimen_support Mitegen
_diffrn_detector                 CCD
_diffrn_measurement_device       
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type  
;
Rigaku Saturn724+ (2x2 bin mode)
;
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_reflns_number            34787
_diffrn_reflns_av_unetI/netI     0.0262
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.069
_diffrn_reflns_theta_max         27.480
_diffrn_reflns_theta_full        27.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             6106
_reflns_number_gt                4981
_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       
;
CrystalClear-SM Expert 3.1 b27 (Rigaku, 2012)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 3.1 b27 (Rigaku, 2012)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 3.1 b27 (Rigaku, 2012)
;

_computing_structure_solution    'SHELXS-97  (Sheldrick, 2007)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_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.

Two phenyl rings were refined using rigid hexagonal restraints, 
with two, slightly different, positions for these two rings.
The ratio between these two positions was 52:48.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0436P)²+1.7984P] 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         6106
_refine_ls_number_parameters     390
_refine_ls_number_restraints     646
_refine_ls_R_factor_all          0.0518
_refine_ls_R_factor_gt           0.0394
_refine_ls_wR_factor_ref         0.1004
_refine_ls_wR_factor_gt          0.0940
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      0.992
_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_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
C1 C 0.52232(6) 0.63822(6) 0.55583(8) 0.0190(2) Uani 1 1 d . U . . .
C2 C 0.58102(6) 0.64878(6) 0.59918(9) 0.0240(3) Uani 1 1 d . U . . .
H2 H 0.6073 0.6856 0.5753 0.029 Uiso 1 1 calc R U . . .
C3 C 0.60302(6) 0.60622(7) 0.67822(10) 0.0296(3) Uani 1 1 d . U . . .
H3 H 0.6439 0.6141 0.7070 0.035 Uiso 1 1 calc R U . . .
C4 C 0.56538(7) 0.55364(7) 0.71313(10) 0.0293(3) Uani 1 1 d . U . . .
H4 H 0.5791 0.5269 0.7693 0.035 Uiso 1 1 calc R U . . .
C5 C 0.50613(6) 0.53824(6) 0.66708(9) 0.0235(3) Uani 1 1 d . U . . .
C6 C 0.46918(7) 0.48040(7) 0.69943(10) 0.0289(3) Uani 1 1 d . U . . .
H6 H 0.4830 0.4539 0.7558 0.035 Uiso 1 1 calc R U . . .
C7 C 0.41448(7) 0.46212(7) 0.65151(11) 0.0308(3) Uani 1 1 d . U . . .
H7 H 0.3903 0.4234 0.6745 0.037 Uiso 1 1 calc R U . . .
C8 C 0.39375(6) 0.50074(6) 0.56771(10) 0.0273(3) Uani 1 1 d . U . . .
H8 H 0.3558 0.4873 0.5340 0.033 Uiso 1 1 calc R U . . .
C9 C 0.42741(6) 0.55782(6) 0.53345(9) 0.0214(2) Uani 1 1 d . U . . .
C10 C 0.48441(6) 0.57950(6) 0.58425(9) 0.0194(2) Uani 1 1 d . U . . .
C11 C 0.49793(6) 0.69277(6) 0.48386(8) 0.0182(2) Uani 1 1 d . U . . .
C12 C 0.40664(6) 0.58713(6) 0.43452(10) 0.0236(3) Uani 1 1 d . U . . .
H12 H 0.4381 0.6073 0.3921 0.028 Uiso 1 1 calc R U . . .
C13 C 0.40376(5) 0.73181(6) 0.75880(9) 0.0190(2) Uani 1 1 d . U . . .
C26 C 0.34190(6) 0.65513(6) 0.86956(9) 0.0209(2) Uani 1 1 d . U . . .
C27 C 0.34847(6) 0.59249(6) 0.81814(10) 0.0255(3) Uani 1 1 d . U . . .
H27 H 0.3792 0.5881 0.7659 0.031 Uiso 1 1 calc R U . . .
C28 C 0.31006(7) 0.53660(7) 0.84350(11) 0.0327(3) Uani 1 1 d . U . . .
H28 H 0.3141 0.4939 0.8078 0.039 Uiso 1 1 calc R U . . .
C29 C 0.26576(7) 0.54210(8) 0.92026(11) 0.0373(3) Uani 1 1 d . U . . .
H29 H 0.2397 0.5034 0.9376 0.045 Uiso 1 1 calc R U . . .
C30 C 0.25976(7) 0.60460(8) 0.97166(11) 0.0367(3) Uani 1 1 d . U . . .
H30 H 0.2295 0.6086 1.0246 0.044 Uiso 1 1 calc R U . . .
C31 C 0.29749(6) 0.66128(7) 0.94648(10) 0.0283(3) Uani 1 1 d . U . . .
H31 H 0.2930 0.7041 0.9817 0.034 Uiso 1 1 calc R U . . .
N1 N 0.45878(5) 0.76712(5) 0.75439(7) 0.0201(2) Uani 1 1 d . U . . .
H1' H 0.4860 0.7609 0.8040 0.024 Uiso 1 1 calc R U . A 1
N2 N 0.37272(5) 0.71591(5) 0.67377(7) 0.0193(2) Uani 1 1 d . U . . .
H2' H 0.3944 0.7051 0.6192 0.023 Uiso 1 1 calc R U . B 1
N3 N 0.38295(5) 0.71260(5) 0.84959(7) 0.0221(2) Uani 1 1 d . U . . .
H3' H 0.3956 0.7375 0.9015 0.027 Uiso 1 1 calc R U . . .
O1 O 0.53446(4) 0.71574(5) 0.41776(6) 0.02400(19) Uani 1 1 d . U . . .
O2 O 0.44022(4) 0.71202(4) 0.49662(6) 0.02026(18) Uani 1 1 d . U . . .
O3 O 0.35189(5) 0.58661(5) 0.40544(7) 0.0334(2) Uani 1 1 d . U . . .
C14A C 0.4763(4) 0.8124(5) 0.6786(6) 0.0204(4) Uani 0.52(4) 1 d G U P C 1
C15A C 0.4341(4) 0.8519(5) 0.6215(8) 0.0350(18) Uani 0.52(4) 1 d G U P C 1
H15A H 0.3895 0.8480 0.6327 0.042 Uiso 0.52(4) 1 calc R U P C 1
C16A C 0.4572(6) 0.8970(5) 0.5481(7) 0.0333(15) Uani 0.52(4) 1 d G U P C 1
H16A H 0.4283 0.9239 0.5091 0.040 Uiso 0.52(4) 1 calc R U P C 1
C17A C 0.5224(7) 0.9025(5) 0.5317(5) 0.0391(17) Uani 0.52(4) 1 d G U P C 1
H17A H 0.5381 0.9334 0.4815 0.047 Uiso 0.52(4) 1 calc R U P C 1
C18A C 0.5646(5) 0.8630(6) 0.5888(9) 0.0368(15) Uani 0.52(4) 1 d G U P C 1
H18A H 0.6092 0.8669 0.5776 0.044 Uiso 0.52(4) 1 calc R U P C 1
C19A C 0.5416(4) 0.8180(5) 0.6622(8) 0.0233(11) Uani 0.52(4) 1 d G U P C 1
H19A H 0.5704 0.7910 0.7012 0.028 Uiso 0.52(4) 1 calc R U P C 1
C14B C 0.4759(4) 0.8177(5) 0.6766(7) 0.0204(4) Uani 0.48(4) 1 d G U P C 2
C15B C 0.4291(3) 0.8602(5) 0.6352(6) 0.0150(12) Uani 0.48(4) 1 d G U P C 2
H15B H 0.3863 0.8568 0.6582 0.018 Uiso 0.48(4) 1 calc R U P C 2
C16B C 0.4448(5) 0.9077(5) 0.5602(6) 0.0298(14) Uani 0.48(4) 1 d G U P C 2
H16B H 0.4128 0.9367 0.5319 0.036 Uiso 0.48(4) 1 calc R U P C 2
C17B C 0.5074(6) 0.9127(6) 0.5265(6) 0.0395(17) Uani 0.48(4) 1 d G U P C 2
H17B H 0.5182 0.9451 0.4752 0.047 Uiso 0.48(4) 1 calc R U P C 2
C18B C 0.5542(5) 0.8702(6) 0.5679(11) 0.0344(18) Uani 0.48(4) 1 d G U P C 2
H18B H 0.5970 0.8736 0.5449 0.041 Uiso 0.48(4) 1 calc R U P C 2
C19B C 0.5385(4) 0.8227(5) 0.6429(11) 0.0264(14) Uani 0.48(4) 1 d G U P C 2
H19B H 0.5705 0.7936 0.6712 0.032 Uiso 0.48(4) 1 calc R U P C 2
C20A C 0.3063(4) 0.7164(7) 0.6710(11) 0.030(2) Uani 0.37(4) 1 d G U P D 1
C21A C 0.2713(5) 0.7664(7) 0.7229(13) 0.0271(16) Uani 0.37(4) 1 d G U P D 1
H21A H 0.2921 0.7969 0.7688 0.033 Uiso 0.37(4) 1 calc R U P D 1
C22A C 0.2060(5) 0.7719(9) 0.7075(15) 0.041(2) Uani 0.37(4) 1 d G U P D 1
H22A H 0.1821 0.8060 0.7429 0.049 Uiso 0.37(4) 1 calc R U P D 1
C23A C 0.1756(4) 0.7274(11) 0.6403(15) 0.039(3) Uani 0.37(4) 1 d G U P D 1
H23A H 0.1309 0.7311 0.6298 0.047 Uiso 0.37(4) 1 calc R U P D 1
C24A C 0.2106(6) 0.6774(10) 0.5884(13) 0.036(2) Uani 0.37(4) 1 d G U P D 1
H24A H 0.1898 0.6469 0.5425 0.043 Uiso 0.37(4) 1 calc R U P D 1
C25A C 0.2759(6) 0.6719(8) 0.6038(12) 0.0353(19) Uani 0.37(4) 1 d G U P D 1
H25A H 0.2999 0.6377 0.5684 0.042 Uiso 0.37(4) 1 calc R U P D 1
C20B C 0.3048(2) 0.7127(3) 0.6602(6) 0.0164(10) Uani 0.63(4) 1 d G U P D 2
C21B C 0.2645(3) 0.7606(3) 0.7061(7) 0.0274(10) Uani 0.63(4) 1 d G U P D 2
H21B H 0.2813 0.7942 0.7515 0.033 Uiso 0.63(4) 1 calc R U P D 2
C22B C 0.1995(3) 0.7595(4) 0.6854(7) 0.0296(12) Uani 0.63(4) 1 d G U P D 2
H22B H 0.1720 0.7922 0.7167 0.036 Uiso 0.63(4) 1 calc R U P D 2
C23B C 0.17489(19) 0.7104(5) 0.6190(7) 0.0327(12) Uani 0.63(4) 1 d G U P D 2
H23B H 0.1305 0.7096 0.6049 0.039 Uiso 0.63(4) 1 calc R U P D 2
C24B C 0.2152(3) 0.6624(5) 0.5732(6) 0.0363(10) Uani 0.63(4) 1 d G U P D 2
H24B H 0.1984 0.6289 0.5278 0.044 Uiso 0.63(4) 1 calc R U P D 2
C25B C 0.2802(3) 0.6636(4) 0.5938(6) 0.0246(9) Uani 0.63(4) 1 d G U P D 2
H25B H 0.3078 0.6308 0.5625 0.030 Uiso 0.63(4) 1 calc R U P D 2


_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
C1 C2 1.3741(17) . ?
C1 C10 1.4297(16) . ?
C1 C11 1.5066(16) . ?
C2 C3 1.4074(18) . ?
C2 H2 0.9500 . ?
C3 C4 1.362(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.4163(19) . ?
C4 H4 0.9500 . ?
C5 C6 1.4200(18) . ?
C5 C10 1.4295(16) . ?
C6 C7 1.358(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.4055(19) . ?
C7 H7 0.9500 . ?
C8 C9 1.3801(17) . ?
C8 H8 0.9500 . ?
C9 C10 1.4343(17) . ?
C9 C12 1.4935(17) . ?
C11 O1 1.2455(14) . ?
C11 O2 1.2768(14) . ?
C12 O3 1.2115(15) . ?
C12 H12 0.9500 . ?
C13 N3 1.3337(15) . ?
C13 N2 1.3381(15) . ?
C13 N1 1.3395(15) . ?
C26 C31 1.3871(17) . ?
C26 C27 1.3890(17) . ?
C26 N3 1.4241(15) . ?
C27 C28 1.3830(18) . ?
C27 H27 0.9500 . ?
C28 C29 1.383(2) . ?
C28 H28 0.9500 . ?
C29 C30 1.385(2) . ?
C29 H29 0.9500 . ?
C30 C31 1.3859(18) . ?
C30 H30 0.9500 . ?
C31 H31 0.9500 . ?
N1 C14A 1.379(6) . ?
N1 C14B 1.462(7) . ?
N1 H1' 0.8800 . ?
N2 C20A 1.393(8) . ?
N2 C20B 1.437(4) . ?
N2 H2' 0.8800 . ?
N3 H3' 0.8800 . ?
C14A C15A 1.3900 . ?
C14A C19A 1.3900 . ?
C15A C16A 1.3900 . ?
C15A H15A 0.9500 . ?
C16A C17A 1.3900 . ?
C16A H16A 0.9500 . ?
C17A C18A 1.3900 . ?
C17A H17A 0.9500 . ?
C18A C19A 1.3900 . ?
C18A H18A 0.9500 . ?
C19A H19A 0.9500 . ?
C14B C15B 1.3900 . ?
C14B C19B 1.3900 . ?
C15B C16B 1.3900 . ?
C15B H15B 0.9500 . ?
C16B C17B 1.3900 . ?
C16B H16B 0.9500 . ?
C17B C18B 1.3900 . ?
C17B H17B 0.9500 . ?
C18B C19B 1.3900 . ?
C18B H18B 0.9500 . ?
C19B H19B 0.9500 . ?
C20A C21A 1.3900 . ?
C20A C25A 1.3900 . ?
C21A C22A 1.3900 . ?
C21A H21A 0.9500 . ?
C22A C23A 1.3900 . ?
C22A H22A 0.9500 . ?
C23A C24A 1.3900 . ?
C23A H23A 0.9500 . ?
C24A C25A 1.3900 . ?
C24A H24A 0.9500 . ?
C25A H25A 0.9500 . ?
C20B C21B 1.3900 . ?
C20B C25B 1.3900 . ?
C21B C22B 1.3900 . ?
C21B H21B 0.9500 . ?
C22B C23B 1.3900 . ?
C22B H22B 0.9500 . ?
C23B C24B 1.3900 . ?
C23B H23B 0.9500 . ?
C24B C25B 1.3900 . ?
C24B H24B 0.9500 . ?
C25B H25B 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 C1 C10 120.27(11) . . ?
C2 C1 C11 117.87(11) . . ?
C10 C1 C11 121.73(10) . . ?
C1 C2 C3 121.36(12) . . ?
C1 C2 H2 119.3 . . ?
C3 C2 H2 119.3 . . ?
C4 C3 C2 119.56(12) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C3 C4 C5 121.08(12) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
C4 C5 C6 120.76(12) . . ?
C4 C5 C10 119.74(11) . . ?
C6 C5 C10 119.44(12) . . ?
C7 C6 C5 121.42(12) . . ?
C7 C6 H6 119.3 . . ?
C5 C6 H6 119.3 . . ?
C6 C7 C8 119.73(12) . . ?
C6 C7 H7 120.1 . . ?
C8 C7 H7 120.1 . . ?
C9 C8 C7 121.40(12) . . ?
C9 C8 H8 119.3 . . ?
C7 C8 H8 119.3 . . ?
C8 C9 C10 120.11(11) . . ?
C8 C9 C12 116.06(11) . . ?
C10 C9 C12 123.18(11) . . ?
C5 C10 C1 117.54(11) . . ?
C5 C10 C9 117.81(11) . . ?
C1 C10 C9 124.62(10) . . ?
O1 C11 O2 125.05(11) . . ?
O1 C11 C1 118.92(10) . . ?
O2 C11 C1 116.03(10) . . ?
O3 C12 C9 123.62(12) . . ?
O3 C12 H12 118.2 . . ?
C9 C12 H12 118.2 . . ?
N3 C13 N2 122.68(10) . . ?
N3 C13 N1 117.46(10) . . ?
N2 C13 N1 119.84(10) . . ?
C31 C26 C27 120.13(11) . . ?
C31 C26 N3 118.50(11) . . ?
C27 C26 N3 121.24(11) . . ?
C28 C27 C26 119.57(12) . . ?
C28 C27 H27 120.2 . . ?
C26 C27 H27 120.2 . . ?
C27 C28 C29 120.77(13) . . ?
C27 C28 H28 119.6 . . ?
C29 C28 H28 119.6 . . ?
C28 C29 C30 119.33(13) . . ?
C28 C29 H29 120.3 . . ?
C30 C29 H29 120.3 . . ?
C29 C30 C31 120.58(13) . . ?
C29 C30 H30 119.7 . . ?
C31 C30 H30 119.7 . . ?
C30 C31 C26 119.61(12) . . ?
C30 C31 H31 120.2 . . ?
C26 C31 H31 120.2 . . ?
C13 N1 C14A 125.5(3) . . ?
C13 N1 C14B 125.3(3) . . ?
C13 N1 H1' 117.3 . . ?
C14A N1 H1' 117.3 . . ?
C13 N2 C20A 120.4(6) . . ?
C13 N2 C20B 126.7(3) . . ?
C13 N2 H2' 119.8 . . ?
C20A N2 H2' 119.8 . . ?
C13 N3 C26 125.45(10) . . ?
C13 N3 H3' 117.3 . . ?
C26 N3 H3' 117.3 . . ?
N1 C14A C15A 124.8(5) . . ?
N1 C14A C19A 115.2(5) . . ?
C15A C14A C19A 120.0 . . ?
C14A C15A C16A 120.0 . . ?
C14A C15A H15A 120.0 . . ?
C16A C15A H15A 120.0 . . ?
C15A C16A C17A 120.0 . . ?
C15A C16A H16A 120.0 . . ?
C17A C16A H16A 120.0 . . ?
C16A C17A C18A 120.0 . . ?
C16A C17A H17A 120.0 . . ?
C18A C17A H17A 120.0 . . ?
C19A C18A C17A 120.0 . . ?
C19A C18A H18A 120.0 . . ?
C17A C18A H18A 120.0 . . ?
C18A C19A C14A 120.0 . . ?
C18A C19A H19A 120.0 . . ?
C14A C19A H19A 120.0 . . ?
C15B C14B C19B 120.0 . . ?
C15B C14B N1 119.7(5) . . ?
C19B C14B N1 120.3(5) . . ?
C16B C15B C14B 120.0 . . ?
C16B C15B H15B 120.0 . . ?
C14B C15B H15B 120.0 . . ?
C17B C16B C15B 120.0 . . ?
C17B C16B H16B 120.0 . . ?
C15B C16B H16B 120.0 . . ?
C16B C17B C18B 120.0 . . ?
C16B C17B H17B 120.0 . . ?
C18B C17B H17B 120.0 . . ?
C17B C18B C19B 120.0 . . ?
C17B C18B H18B 120.0 . . ?
C19B C18B H18B 120.0 . . ?
C18B C19B C14B 120.0 . . ?
C18B C19B H19B 120.0 . . ?
C14B C19B H19B 120.0 . . ?
C21A C20A C25A 120.0 . . ?
C21A C20A N2 121.3(6) . . ?
C25A C20A N2 118.1(6) . . ?
C22A C21A C20A 120.0 . . ?
C22A C21A H21A 120.0 . . ?
C20A C21A H21A 120.0 . . ?
C21A C22A C23A 120.0 . . ?
C21A C22A H22A 120.0 . . ?
C23A C22A H22A 120.0 . . ?
C24A C23A C22A 120.0 . . ?
C24A C23A H23A 120.0 . . ?
C22A C23A H23A 120.0 . . ?
C23A C24A C25A 120.0 . . ?
C23A C24A H24A 120.0 . . ?
C25A C24A H24A 120.0 . . ?
C24A C25A C20A 120.0 . . ?
C24A C25A H25A 120.0 . . ?
C20A C25A H25A 120.0 . . ?
C21B C20B C25B 120.0 . . ?
C21B C20B N2 121.3(3) . . ?
C25B C20B N2 118.5(3) . . ?
C20B C21B C22B 120.0 . . ?
C20B C21B H21B 120.0 . . ?
C22B C21B H21B 120.0 . . ?
C23B C22B C21B 120.0 . . ?
C23B C22B H22B 120.0 . . ?
C21B C22B H22B 120.0 . . ?
C24B C23B C22B 120.0 . . ?
C24B C23B H23B 120.0 . . ?
C22B C23B H23B 120.0 . . ?
C25B C24B C23B 120.0 . . ?
C25B C24B H24B 120.0 . . ?
C23B C24B H24B 120.0 . . ?
C24B C25B C20B 120.0 . . ?
C24B C25B H25B 120.0 . . ?
C20B C25B H25B 120.0 . . ?

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 H2' O2 0.88 1.89 2.7459(12) 162.2 .
N3 H3' O2 0.88 1.85 2.7099(13) 166.9 8_576
N1 H1' O1 0.88 1.87 2.7074(13) 157.3 8_576

_refine_diff_density_max         0.234
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.037

_shelxl_version_number           2014-3

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol'
####################################################################### 
# 
# 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_Me4guan
_database_code_depnum_ccdc_archive 'CCDC 1435394'
_audit_update_record             
;
2015-11-05 deposited with the CCDC.
2016-01-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
"N,N,N',N'-tetramethylguanidinium naphthalaldehydate,(Me2N)2CNH2.15"
_chemical_name_common            ?
_chemical_melting_point          404-406
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H21 N3 O3'
_chemical_formula_weight         315.37

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                   9.0149(5)
_cell_length_b                   9.7808(5)
_cell_length_c                   18.7439(11)
_cell_angle_alpha                90
_cell_angle_beta                 102.981(5)
_cell_angle_gamma                90
_cell_volume                     1610.47(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    110(2)
_cell_measurement_reflns_used    2533
_cell_measurement_theta_min      3.4790
_cell_measurement_theta_max      27.9970


_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_F_000             672
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3497
_exptl_crystal_size_mid          0.1832
_exptl_crystal_size_min          0.1279
_exptl_absorpt_coefficient_mu    0.091
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.974
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_correction_type   analytical
_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)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           
;
Crystals grown from THF in a desiccator, coated in oil and measured at 110 K.
The crystals decomposed at room temperature if exposed to water.
;

_diffrn_ambient_temperature      110(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Sapphire3
_diffrn_detector_area_resol_mean 15.9832
_diffrn_reflns_number            7462
_diffrn_reflns_av_unetI/netI     0.0407
_diffrn_reflns_av_R_equivalents  0.0238
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.052
_diffrn_reflns_theta_max         28.182
_diffrn_reflns_theta_full        26.000
_diffrn_measured_fraction_theta_max 0.835
_diffrn_measured_fraction_theta_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.835
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.835
_diffrn_reflns_point_group_measured_fraction_full 0.974
_reflns_number_total             3294
_reflns_number_gt                2697
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_solution    SHELXS-2013
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_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)+(0.0304P)²+0.6632P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3294
_refine_ls_number_parameters     224
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0691
_refine_ls_R_factor_gt           0.0527
_refine_ls_wR_factor_ref         0.1069
_refine_ls_wR_factor_gt          0.1008
_refine_ls_goodness_of_fit_ref   1.154
_refine_ls_restrained_S_all      1.154
_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 0.80188(14) 0.44025(12) 0.00752(7) 0.0226(3) Uani 1 1 d . . . . .
O2 O 0.71302(15) 0.25020(12) 0.04913(7) 0.0267(3) Uani 1 1 d . . . . .
O3 O 1.18102(15) 0.37897(16) 0.14925(8) 0.0411(4) Uani 1 1 d . . . . .
N1 N 1.20871(17) 0.14794(15) -0.06158(8) 0.0202(3) Uani 1 1 d . . . . .
N2 N 0.94731(16) 0.11682(14) -0.09920(8) 0.0196(3) Uani 1 1 d . . . . .
N3 N 1.0435(2) 0.30982(16) -0.03411(8) 0.0200(3) Uani 1 1 d . . . . .
H3A H 1.118(2) 0.378(2) -0.0256(11) 0.037(6) Uiso 1 1 d . . . . .
H3B H 0.953(3) 0.335(2) -0.0262(11) 0.037(6) Uiso 1 1 d . . . . .
C1 C 0.70300(19) 0.45804(17) 0.11306(9) 0.0165(4) Uani 1 1 d . . . . .
C2 C 0.5517(2) 0.48026(18) 0.10994(10) 0.0218(4) Uani 1 1 d . . . . .
H2 H 0.4782 0.4363 0.0727 0.026 Uiso 1 1 calc R U . . .
C3 C 0.5014(2) 0.56564(19) 0.15975(11) 0.0282(5) Uani 1 1 d . . . . .
H3 H 0.3956 0.5770 0.1570 0.034 Uiso 1 1 calc R U . . .
C4 C 0.6055(2) 0.63207(19) 0.21198(11) 0.0295(5) Uani 1 1 d . . . . .
H4 H 0.5717 0.6928 0.2446 0.035 Uiso 1 1 calc R U . . .
C5 C 0.7635(2) 0.61211(18) 0.21855(10) 0.0225(4) Uani 1 1 d . . . . .
C6 C 0.8707(3) 0.6837(2) 0.27221(11) 0.0317(5) Uani 1 1 d . . . . .
H6 H 0.8352 0.7445 0.3042 0.038 Uiso 1 1 calc R U . . .
C7 C 1.0233(2) 0.6678(2) 0.27935(10) 0.0328(5) Uani 1 1 d . . . . .
H7 H 1.0933 0.7206 0.3140 0.039 Uiso 1 1 calc R U . . .
C8 C 1.0755(2) 0.57273(19) 0.23501(10) 0.0255(4) Uani 1 1 d . . . . .
H8 H 1.1820 0.5591 0.2412 0.031 Uiso 1 1 calc R U . . .
C9 C 0.97660(19) 0.49800(17) 0.18241(9) 0.0185(4) Uani 1 1 d . . . . .
C10 C 0.81560(19) 0.52023(17) 0.17028(9) 0.0164(4) Uani 1 1 d . . . . .
C11 C 0.74251(18) 0.37408(17) 0.05181(9) 0.0168(4) Uani 1 1 d . . . . .
C12 C 1.0457(2) 0.3884(2) 0.14595(10) 0.0233(4) Uani 1 1 d . . . . .
H12 H 0.977(2) 0.315(2) 0.1212(10) 0.028(5) Uiso 1 1 d . . . . .
C13 C 1.0668(2) 0.19291(17) -0.06494(9) 0.0169(4) Uani 1 1 d . . . . .
C14 C 1.3381(2) 0.2065(2) -0.00887(11) 0.0280(5) Uani 1 1 d . . . . .
H14A H 1.3036 0.2405 0.0339 0.042 Uiso 1 1 calc R U . . .
H14B H 1.3812 0.2822 -0.0319 0.042 Uiso 1 1 calc R U . . .
H14C H 1.4159 0.1360 0.0066 0.042 Uiso 1 1 calc R U . . .
C15 C 1.2498(2) 0.06840(19) -0.12057(11) 0.0264(4) Uani 1 1 d . . . . .
H15A H 1.2793 -0.0242 -0.1030 0.040 Uiso 1 1 calc R U . . .
H15B H 1.3352 0.1126 -0.1358 0.040 Uiso 1 1 calc R U . . .
H15C H 1.1622 0.0636 -0.1623 0.040 Uiso 1 1 calc R U . . .
C16 C 0.9520(2) -0.03224(18) -0.10015(11) 0.0259(4) Uani 1 1 d . . . . .
H16A H 1.0492 -0.0639 -0.0701 0.039 Uiso 1 1 calc R U . . .
H16B H 0.9417 -0.0641 -0.1506 0.039 Uiso 1 1 calc R U . . .
H16C H 0.8682 -0.0688 -0.0805 0.039 Uiso 1 1 calc R U . . .
C17 C 0.7951(2) 0.1768(2) -0.11868(11) 0.0273(4) Uani 1 1 d . . . . .
H17A H 0.8028 0.2733 -0.1315 0.041 Uiso 1 1 calc R U . . .
H17B H 0.7467 0.1697 -0.0769 0.041 Uiso 1 1 calc R U . . .
H17C H 0.7337 0.1277 -0.1607 0.041 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 C11 1.263(2) . ?
O2 C11 1.239(2) . ?
O3 C12 1.211(2) . ?
N1 C13 1.341(2) . ?
N1 C14 1.465(2) . ?
N1 C15 1.466(2) . ?
N2 C13 1.348(2) . ?
N2 C16 1.459(2) . ?
N2 C17 1.461(2) . ?
N3 C13 1.319(2) . ?
C1 C2 1.370(2) . ?
C1 C10 1.436(2) . ?
C1 C11 1.518(2) . ?
C2 C3 1.402(3) . ?
C3 C4 1.360(3) . ?
C4 C5 1.415(3) . ?
C5 C6 1.414(3) . ?
C5 C10 1.427(2) . ?
C6 C7 1.360(3) . ?
C7 C8 1.398(3) . ?
C8 C9 1.381(2) . ?
C9 C10 1.434(2) . ?
C9 C12 1.482(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
C13 N1 C14 120.65(15) . . ?
C13 N1 C15 122.59(15) . . ?
C14 N1 C15 114.75(15) . . ?
C13 N2 C16 122.39(15) . . ?
C13 N2 C17 120.17(15) . . ?
C16 N2 C17 115.24(15) . . ?
C2 C1 C10 119.66(16) . . ?
C2 C1 C11 117.03(15) . . ?
C10 C1 C11 123.21(15) . . ?
C1 C2 C3 122.28(18) . . ?
C4 C3 C2 119.35(18) . . ?
C3 C4 C5 121.01(17) . . ?
C6 C5 C4 120.48(18) . . ?
C6 C5 C10 119.55(17) . . ?
C4 C5 C10 119.96(17) . . ?
C7 C6 C5 121.87(18) . . ?
C6 C7 C8 119.05(18) . . ?
C9 C8 C7 121.82(18) . . ?
C8 C9 C10 120.06(17) . . ?
C8 C9 C12 116.20(16) . . ?
C10 C9 C12 123.50(15) . . ?
C5 C10 C9 117.40(16) . . ?
C5 C10 C1 117.54(16) . . ?
C9 C10 C1 125.06(15) . . ?
O2 C11 O1 126.40(17) . . ?
O2 C11 C1 118.36(15) . . ?
O1 C11 C1 115.23(15) . . ?
O3 C12 C9 123.68(18) . . ?
N3 C13 N1 120.54(16) . . ?
N3 C13 N2 119.90(16) . . ?
N1 C13 N2 119.56(15) . . ?

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
N3 H3A O1 0.93(2) 1.92(2) 2.803(2) 157.0(18) 3_765
N3 H3B O1 0.90(2) 1.92(2) 2.783(2) 160(2) .


_refine_diff_density_max         0.215
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.042

_shelxl_version_number           2013-4

_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: THF'
_chemical_properties_physical    Moisture-sensitive
####################################################################### 
# 
# 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_DMABSB
_database_code_depnum_ccdc_archive 'CCDC 1435395'
_audit_update_record             
;
2015-11-05 deposited with the CCDC.
2016-01-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
'4-dimethylaminopyridium naphthalaldehydate.naphthalaldehydic acidDMAP.14.15'
_chemical_name_common            ?
_chemical_melting_point          416-417
_chemical_formula_moiety         ?
_chemical_formula_sum            'C31 H26 N2 O6'
_chemical_formula_weight         522.54

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                   15.3271(4)
_cell_length_b                   8.3575(3)
_cell_length_c                   20.6960(6)
_cell_angle_alpha                90
_cell_angle_beta                 105.966(3)
_cell_angle_gamma                90
_cell_volume                     2548.81(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4839
_cell_measurement_theta_min      3.5960
_cell_measurement_theta_max      28.8000


_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_F_000             1104
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3790
_exptl_crystal_size_mid          0.3061
_exptl_crystal_size_min          0.1894
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_min  0.974
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_correction_type   analytical
_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)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Sapphire3
_diffrn_detector_area_resol_mean 15.9832
_diffrn_reflns_number            14522
_diffrn_reflns_av_unetI/netI     0.0461
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         2.953
_diffrn_reflns_theta_max         29.524
_diffrn_reflns_theta_full        27.500
_diffrn_measured_fraction_theta_max 0.848
_diffrn_measured_fraction_theta_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.848
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.848
_diffrn_reflns_point_group_measured_fraction_full 0.971
_reflns_number_total             6036
_reflns_number_gt                4920
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_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)+(0.0541P)²+1.2137P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6036
_refine_ls_number_parameters     366
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0806
_refine_ls_R_factor_gt           0.0626
_refine_ls_wR_factor_ref         0.1414
_refine_ls_wR_factor_gt          0.1327
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_restrained_S_all      1.098
_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 0.00426(11) -0.09934(17) 0.19853(7) 0.0376(4) Uani 1 1 d . . . . .
O2 O 0.01182(9) -0.00215(16) 0.10064(6) 0.0295(3) Uani 1 1 d . . . . .
O3 O -0.21533(12) 0.0724(3) 0.19785(11) 0.0709(6) Uani 1 1 d . . . . .
O4 O 0.28650(9) 0.13654(18) 0.09624(7) 0.0346(3) Uani 1 1 d . . . . .
O5 O 0.33624(9) 0.37193(17) 0.13759(6) 0.0302(3) Uani 1 1 d . . . . .
O6 O 0.48823(9) 0.43927(17) 0.17187(7) 0.0293(3) Uani 1 1 d . . . . .
H61 H 0.4908(17) 0.428(3) 0.2162(15) 0.060(8) Uiso 1 1 d . . . . .
N1 N -0.06415(10) -0.2738(2) 0.04880(8) 0.0248(3) Uani 1 1 d . . . . .
H1 H -0.0388(15) -0.181(3) 0.0685(11) 0.036(6) Uiso 1 1 d . . . . .
N2 N -0.16841(11) -0.69603(19) -0.04230(8) 0.0304(4) Uani 1 1 d . . . . .
C1 C 0.05493(11) 0.1687(2) 0.19446(8) 0.0184(3) Uani 1 1 d . . . . .
C2 C 0.14352(11) 0.2054(2) 0.19762(8) 0.0218(4) Uani 1 1 d . . . . .
H2 H 0.1776 0.1337 0.1785 0.026 Uiso 1 1 calc R U . . .
C3 C 0.18491(11) 0.3465(2) 0.22851(9) 0.0246(4) Uani 1 1 d . . . . .
H3 H 0.2465 0.3685 0.2308 0.030 Uiso 1 1 calc R U . . .
C4 C 0.13632(12) 0.4509(2) 0.25497(9) 0.0234(4) Uani 1 1 d . . . . .
H4 H 0.1643 0.5462 0.2758 0.028 Uiso 1 1 calc R U . . .
C5 C 0.04428(11) 0.4197(2) 0.25188(8) 0.0204(4) Uani 1 1 d . . . . .
C6 C -0.00489(13) 0.5322(2) 0.27920(10) 0.0288(4) Uani 1 1 d . . . . .
H6 H 0.0242 0.6274 0.2992 0.035 Uiso 1 1 calc R U . . .
C7 C -0.09288(14) 0.5059(3) 0.27716(11) 0.0349(5) Uani 1 1 d . . . . .
H7 H -0.1250 0.5818 0.2961 0.042 Uiso 1 1 calc R U . . .
C8 C -0.13625(12) 0.3667(3) 0.24711(10) 0.0307(4) Uani 1 1 d . . . . .
H8 H -0.1980 0.3498 0.2457 0.037 Uiso 1 1 calc R U . . .
C9 C -0.09218(11) 0.2536(2) 0.21956(8) 0.0217(4) Uani 1 1 d . . . . .
C10 C 0.00157(10) 0.2769(2) 0.22120(8) 0.0170(3) Uani 1 1 d . . . . .
C11 C 0.02076(11) 0.0093(2) 0.16281(9) 0.0208(4) Uani 1 1 d . . . . .
C12 C -0.14885(12) 0.1181(3) 0.18512(11) 0.0317(5) Uani 1 1 d . . . . .
H12 H -0.1382(15) 0.073(3) 0.1442(12) 0.044(7) Uiso 1 1 d . . . . .
C21 C 0.33352(11) 0.3139(2) 0.02239(9) 0.0227(4) Uani 1 1 d . . . . .
C22 C 0.30631(13) 0.2159(3) -0.03260(10) 0.0313(4) Uani 1 1 d . . . . .
H22 H 0.2834 0.1122 -0.0280 0.038 Uiso 1 1 calc R U . . .
C23 C 0.31226(15) 0.2682(3) -0.09585(10) 0.0391(5) Uani 1 1 d . . . . .
H23 H 0.2941 0.1993 -0.1337 0.047 Uiso 1 1 calc R U . . .
C24 C 0.34408(14) 0.4182(3) -0.10303(10) 0.0366(5) Uani 1 1 d . . . . .
H24 H 0.3469 0.4529 -0.1461 0.044 Uiso 1 1 calc R U . . .
C25 C 0.37284(12) 0.5227(3) -0.04742(10) 0.0292(4) Uani 1 1 d . . . . .
C26 C 0.40644(14) 0.6785(3) -0.05208(11) 0.0377(5) Uani 1 1 d . . . . .
H26 H 0.4100 0.7176 -0.0944 0.045 Uiso 1 1 calc R U . . .
C27 C 0.43368(15) 0.7728(3) 0.00329(12) 0.0414(5) Uani 1 1 d . . . . .
H27 H 0.4553 0.8778 -0.0009 0.050 Uiso 1 1 calc R U . . .
C28 C 0.43033(14) 0.7171(3) 0.06694(11) 0.0344(5) Uani 1 1 d . . . . .
H28 H 0.4496 0.7845 0.1052 0.041 Uiso 1 1 calc R U . . .
C29 C 0.39947(12) 0.5667(2) 0.07362(9) 0.0250(4) Uani 1 1 d . . . . .
C30 C 0.36852(11) 0.4681(2) 0.01662(9) 0.0226(4) Uani 1 1 d . . . . .
C31 C 0.31865(11) 0.2635(2) 0.08717(9) 0.0249(4) Uani 1 1 d . . . . .
C32 C 0.40241(12) 0.4989(2) 0.14130(9) 0.0256(4) Uani 1 1 d . . . . .
H32 H 0.3892 0.5870 0.1699 0.031 Uiso 1 1 calc R U . . .
C41 C -0.07733(11) -0.2928(2) -0.01794(9) 0.0231(4) Uani 1 1 d . . . . .
H41 H -0.0620 -0.2079 -0.0433 0.028 Uiso 1 1 calc R U . . .
C42 C -0.11188(11) -0.4300(2) -0.04955(9) 0.0224(4) Uani 1 1 d . . . . .
H42 H -0.1204 -0.4403 -0.0966 0.027 Uiso 1 1 calc R U . . .
C43 C -0.13526(11) -0.5580(2) -0.01290(9) 0.0227(4) Uani 1 1 d . . . . .
C44 C -0.12127(12) -0.5324(2) 0.05717(9) 0.0269(4) Uani 1 1 d . . . . .
H44 H -0.1365 -0.6138 0.0842 0.032 Uiso 1 1 calc R U . . .
C45 C -0.08615(12) -0.3915(2) 0.08545(9) 0.0274(4) Uani 1 1 d . . . . .
H45 H -0.0770 -0.3760 0.1323 0.033 Uiso 1 1 calc R U . . .
C46 C -0.18466(15) -0.7199(3) -0.11467(11) 0.0382(5) Uani 1 1 d . . . . .
H46C H -0.2196 -0.6296 -0.1389 0.057 Uiso 1 1 calc R U . . .
H46A H -0.2188 -0.8193 -0.1281 0.057 Uiso 1 1 calc R U . . .
H46B H -0.1264 -0.7270 -0.1255 0.057 Uiso 1 1 calc R U . . .
C47 C -0.18661(17) -0.8298(3) -0.00260(13) 0.0462(6) Uani 1 1 d . . . . .
H47A H -0.1303 -0.8612 0.0307 0.069 Uiso 1 1 calc R U . . .
H47B H -0.2100 -0.9205 -0.0323 0.069 Uiso 1 1 calc R U . . .
H47C H -0.2317 -0.7975 0.0205 0.069 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 C11 1.240(2) . ?
O2 C11 1.260(2) . ?
O3 C12 1.184(2) . ?
O4 C31 1.206(2) . ?
O5 C31 1.352(2) . ?
O5 C32 1.455(2) . ?
O6 C32 1.386(2) . ?
N1 C45 1.341(2) . ?
N1 C41 1.349(2) . ?
N2 C43 1.337(2) . ?
N2 C47 1.459(3) . ?
N2 C46 1.463(3) . ?
C1 C2 1.376(2) . ?
C1 C10 1.429(2) . ?
C1 C11 1.513(2) . ?
C2 C3 1.406(3) . ?
C3 C4 1.357(3) . ?
C4 C5 1.419(2) . ?
C5 C6 1.416(3) . ?
C5 C10 1.424(2) . ?
C6 C7 1.356(3) . ?
C7 C8 1.398(3) . ?
C8 C9 1.373(3) . ?
C9 C10 1.441(2) . ?
C9 C12 1.485(3) . ?
C21 C22 1.371(3) . ?
C21 C30 1.414(3) . ?
C21 C31 1.482(2) . ?
C22 C23 1.407(3) . ?
C23 C24 1.368(3) . ?
C24 C25 1.415(3) . ?
C25 C26 1.413(3) . ?
C25 C30 1.421(3) . ?
C26 C27 1.359(3) . ?
C27 C28 1.411(3) . ?
C28 C29 1.364(3) . ?
C29 C30 1.410(3) . ?
C29 C32 1.500(3) . ?
C41 C42 1.354(3) . ?
C42 C43 1.414(3) . ?
C43 C44 1.423(3) . ?
C44 C45 1.358(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
C31 O5 C32 121.17(14) . . ?
C45 N1 C41 120.16(17) . . ?
C43 N2 C47 120.81(17) . . ?
C43 N2 C46 121.33(17) . . ?
C47 N2 C46 117.82(17) . . ?
C2 C1 C10 120.19(16) . . ?
C2 C1 C11 115.89(15) . . ?
C10 C1 C11 123.91(14) . . ?
C1 C2 C3 121.63(16) . . ?
C4 C3 C2 119.59(16) . . ?
C3 C4 C5 120.86(17) . . ?
C6 C5 C4 119.45(17) . . ?
C6 C5 C10 120.30(16) . . ?
C4 C5 C10 120.25(16) . . ?
C7 C6 C5 120.93(18) . . ?
C6 C7 C8 119.73(18) . . ?
C9 C8 C7 121.95(17) . . ?
C8 C9 C10 119.91(17) . . ?
C8 C9 C12 115.76(16) . . ?
C10 C9 C12 124.18(16) . . ?
C5 C10 C1 117.46(14) . . ?
C5 C10 C9 117.17(15) . . ?
C1 C10 C9 125.36(16) . . ?
O1 C11 O2 124.78(17) . . ?
O1 C11 C1 119.33(15) . . ?
O2 C11 C1 115.90(15) . . ?
O3 C12 C9 124.4(2) . . ?
C22 C21 C30 120.70(17) . . ?
C22 C21 C31 119.61(17) . . ?
C30 C21 C31 119.47(16) . . ?
C21 C22 C23 120.26(19) . . ?
C24 C23 C22 120.2(2) . . ?
C23 C24 C25 121.19(19) . . ?
C26 C25 C24 123.43(19) . . ?
C26 C25 C30 118.13(18) . . ?
C24 C25 C30 118.44(19) . . ?
C27 C26 C25 120.70(19) . . ?
C26 C27 C28 120.9(2) . . ?
C29 C28 C27 120.1(2) . . ?
C28 C29 C30 120.02(18) . . ?
C28 C29 C32 121.39(18) . . ?
C30 C29 C32 118.51(17) . . ?
C29 C30 C21 120.69(17) . . ?
C29 C30 C25 120.09(17) . . ?
C21 C30 C25 119.22(17) . . ?
O4 C31 O5 118.22(17) . . ?
O4 C31 C21 124.20(18) . . ?
O5 C31 C21 117.39(16) . . ?
O6 C32 O5 108.80(15) . . ?
O6 C32 C29 110.06(15) . . ?
O5 C32 C29 112.63(14) . . ?
N1 C41 C42 121.54(17) . . ?
C41 C42 C43 120.33(16) . . ?
N2 C43 C42 121.96(17) . . ?
N2 C43 C44 121.72(17) . . ?
C42 C43 C44 116.32(16) . . ?
C45 C44 C43 120.06(17) . . ?
N1 C45 C44 121.58(17) . . ?

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
O6 H61 O1 0.91(3) 1.76(3) 2.6724(19) 179(3) 2
N1 H1 O2 0.91(2) 1.73(3) 2.640(2) 176(2) .
C41 H41 O2 0.95 2.36 3.310(2) 175.3 3

_refine_diff_density_max         0.379
_refine_diff_density_min         -0.362
_refine_diff_density_rms         0.054

_shelxl_version_number           2013-4

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetonitrile'
####################################################################### 
# 
# 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_morpholine_adduct
_database_code_depnum_ccdc_archive 'CCDC 1435396'
_audit_update_record             
;
2015-11-05 deposited with the CCDC.
2016-01-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
3-(4-Morpholinyl)-1H,3H-naphtho[1,8-cd]pyran-1-one, A
;
_chemical_name_common            ?
_chemical_melting_point          431-433
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H15 N O3'
_chemical_formula_weight         269.29

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   8.6000(4)
_cell_length_b                   8.6685(4)
_cell_length_c                   9.6470(6)
_cell_angle_alpha                101.959(7)
_cell_angle_beta                 106.112(8)
_cell_angle_gamma                105.087(7)
_cell_volume                     636.12(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8010
_cell_measurement_theta_min      3.7
_cell_measurement_theta_max      27.5

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.406
_exptl_crystal_F_000             284
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.098
_shelx_estimated_absorpt_T_min   0.967
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.801
_exptl_absorpt_process_details   
;
CrystalClear-SM Expert 2.0 r11 (Rigaku, 2011)
;
_exptl_special_details           ?

_diffrn_ambient_temperature      100(2)
_diffrn_source_power             2.5
_diffrn_source_voltage           45.0
_diffrn_source_current           55.0
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           'Mo K\a'
_diffrn_source                   'Rotating Anode'
_diffrn_radiation_monochromator  Confocal
_diffrn_measurement_specimen_support MiTeGen
_diffrn_detector                 CCD
_diffrn_measurement_device       
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type  
;
Rigaku Saturn724+ (2x2 bin mode)
;
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measurement_method       'profile data from ω-scans'

_diffrn_reflns_number            8547
_diffrn_reflns_av_unetI/netI     0.0345
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.672
_diffrn_reflns_theta_max         27.472
_diffrn_reflns_theta_full        27.500
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.986
_reflns_number_total             2889
_reflns_number_gt                2569
_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       
;
CrystalClear-SM Expert 3.1 b27 (Rigaku, 2012)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 3.1 b27 (Rigaku, 2012)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 3.1 b27 (Rigaku, 2012)
;
_computing_structure_solution    'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_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)+(0.0531P)²+0.1481P] 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         2889
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0403
_refine_ls_R_factor_gt           0.0363
_refine_ls_wR_factor_ref         0.1047
_refine_ls_wR_factor_gt          0.1020
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_restrained_S_all      1.073
_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_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
C1 C 0.09385(13) 0.67783(13) 0.31428(11) 0.0158(2) Uani 1 1 d . . . . .
C2 C 0.24755(13) 0.64319(12) 0.29372(11) 0.0153(2) Uani 1 1 d . . . . .
C3 C 0.23367(13) 0.54286(13) 0.15674(11) 0.0175(2) Uani 1 1 d . . . . .
H3 H 0.1265 0.4983 0.0754 0.021 Uiso 1 1 calc R U . . .
C4 C 0.37766(14) 0.50605(13) 0.13671(12) 0.0191(2) Uani 1 1 d . . . . .
H4 H 0.3689 0.4431 0.0400 0.023 Uiso 1 1 calc R U . . .
C5 C 0.53024(13) 0.56043(13) 0.25567(12) 0.0181(2) Uani 1 1 d . . . . .
H5 H 0.6258 0.5334 0.2408 0.022 Uiso 1 1 calc R U . . .
C6 C 0.54722(13) 0.65669(12) 0.40098(11) 0.0160(2) Uani 1 1 d . . . . .
C7 C 0.69995(13) 0.70867(13) 0.52828(12) 0.0183(2) Uani 1 1 d . . . . .
H7 H 0.7948 0.6764 0.5186 0.022 Uiso 1 1 calc R U . . .
C8 C 0.71206(13) 0.80538(14) 0.66571(12) 0.0197(2) Uani 1 1 d . . . . .
H8 H 0.8130 0.8354 0.7516 0.024 Uiso 1 1 calc R U . . .
C9 C 0.57439(13) 0.86033(14) 0.67943(12) 0.0190(2) Uani 1 1 d . . . . .
H9 H 0.5861 0.9319 0.7735 0.023 Uiso 1 1 calc R U . . .
C10 C 0.42401(13) 0.81165(13) 0.55852(11) 0.0158(2) Uani 1 1 d . . . . .
C11 C 0.40536(12) 0.70420(12) 0.41782(11) 0.0146(2) Uani 1 1 d . . . . .
C12 C 0.28420(12) 0.88441(13) 0.56706(11) 0.0155(2) Uani 1 1 d . . . . .
H12 H 0.3159 0.9949 0.5470 0.019 Uiso 1 1 calc R U . . .
C13 C 0.16893(13) 1.02550(13) 0.73849(12) 0.0169(2) Uani 1 1 d . . . . .
H13A H 0.0466 0.9698 0.6727 0.020 Uiso 1 1 calc R U . . .
H13B H 0.2147 1.1298 0.7143 0.020 Uiso 1 1 calc R U . . .
C14 C 0.18416(14) 1.06651(13) 0.90379(12) 0.0197(2) Uani 1 1 d . . . . .
H14A H 0.3056 1.1304 0.9682 0.024 Uiso 1 1 calc R U . . .
H14B H 0.1147 1.1382 0.9220 0.024 Uiso 1 1 calc R U . . .
C15 C 0.22332(14) 0.81200(14) 0.91875(12) 0.0201(2) Uani 1 1 d . . . . .
H15A H 0.1812 0.7099 0.9473 0.024 Uiso 1 1 calc R U . . .
H15B H 0.3459 0.8704 0.9827 0.024 Uiso 1 1 calc R U . . .
C16 C 0.20715(13) 0.76254(13) 0.75365(11) 0.0176(2) Uani 1 1 d . . . . .
H16A H 0.2769 0.6904 0.7379 0.021 Uiso 1 1 calc R U . . .
H16B H 0.0857 0.6985 0.6894 0.021 Uiso 1 1 calc R U . . .
N4 N 0.26727(11) 0.91398(11) 0.71154(9) 0.01523(19) Uani 1 1 d . . . . .
O1 O -0.04858(9) 0.61713(10) 0.21808(8) 0.02107(19) Uani 1 1 d . . . . .
O2 O 0.11316(9) 0.77668(10) 0.44966(8) 0.01933(18) Uani 1 1 d . . . . .
O3 O 0.12715(10) 0.91894(10) 0.94555(8) 0.02100(19) 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
C1 O1 1.2123(13) . ?
C1 O2 1.3452(12) . ?
C1 C2 1.4846(14) . ?
C2 C3 1.3780(14) . ?
C2 C11 1.4202(14) . ?
C3 C4 1.4090(14) . ?
C3 H3 0.9500 . ?
C4 C5 1.3708(15) . ?
C4 H4 0.9500 . ?
C5 C6 1.4215(14) . ?
C5 H5 0.9500 . ?
C6 C7 1.4155(15) . ?
C6 C11 1.4242(14) . ?
C7 C8 1.3743(15) . ?
C7 H7 0.9500 . ?
C8 C9 1.4144(14) . ?
C8 H8 0.9500 . ?
C9 C10 1.3732(15) . ?
C9 H9 0.9500 . ?
C10 C11 1.4188(13) . ?
C10 C12 1.5095(14) . ?
C12 N4 1.4190(12) . ?
C12 O2 1.4968(12) . ?
C12 H12 1.0000 . ?
C13 N4 1.4700(12) . ?
C13 C14 1.5203(14) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 O3 1.4268(13) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 O3 1.4243(13) . ?
C15 C16 1.5175(13) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 N4 1.4628(13) . ?
C16 H16A 0.9900 . ?
C16 H16B 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
O1 C1 O2 118.43(9) . . ?
O1 C1 C2 123.68(9) . . ?
O2 C1 C2 117.82(9) . . ?
C3 C2 C11 120.13(9) . . ?
C3 C2 C1 119.76(9) . . ?
C11 C2 C1 119.98(9) . . ?
C2 C3 C4 120.35(9) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C5 C4 C3 120.51(9) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C4 C5 C6 120.82(9) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C7 C6 C5 122.56(9) . . ?
C7 C6 C11 119.03(9) . . ?
C5 C6 C11 118.40(9) . . ?
C8 C7 C6 120.53(10) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C7 C8 C9 120.10(10) . . ?
C7 C8 H8 120.0 . . ?
C9 C8 H8 120.0 . . ?
C10 C9 C8 120.89(9) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C9 C10 C11 119.85(9) . . ?
C9 C10 C12 121.17(9) . . ?
C11 C10 C12 118.67(9) . . ?
C10 C11 C2 121.07(9) . . ?
C10 C11 C6 119.41(9) . . ?
C2 C11 C6 119.52(9) . . ?
N4 C12 O2 108.90(8) . . ?
N4 C12 C10 113.02(8) . . ?
O2 C12 C10 112.24(8) . . ?
N4 C12 H12 107.5 . . ?
O2 C12 H12 107.5 . . ?
C10 C12 H12 107.5 . . ?
N4 C13 C14 108.77(8) . . ?
N4 C13 H13A 109.9 . . ?
C14 C13 H13A 109.9 . . ?
N4 C13 H13B 109.9 . . ?
C14 C13 H13B 109.9 . . ?
H13A C13 H13B 108.3 . . ?
O3 C14 C13 111.86(8) . . ?
O3 C14 H14A 109.2 . . ?
C13 C14 H14A 109.2 . . ?
O3 C14 H14B 109.2 . . ?
C13 C14 H14B 109.2 . . ?
H14A C14 H14B 107.9 . . ?
O3 C15 C16 111.15(9) . . ?
O3 C15 H15A 109.4 . . ?
C16 C15 H15A 109.4 . . ?
O3 C15 H15B 109.4 . . ?
C16 C15 H15B 109.4 . . ?
H15A C15 H15B 108.0 . . ?
N4 C16 C15 109.13(8) . . ?
N4 C16 H16A 109.9 . . ?
C15 C16 H16A 109.9 . . ?
N4 C16 H16B 109.9 . . ?
C15 C16 H16B 109.9 . . ?
H16A C16 H16B 108.3 . . ?
C12 N4 C16 114.59(8) . . ?
C12 N4 C13 114.68(8) . . ?
C16 N4 C13 110.79(8) . . ?
C1 O2 C12 123.66(8) . . ?
C15 O3 C14 110.58(8) . . ?

_refine_diff_density_max         0.310
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.043

_shelxl_version_number           2013-4


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol'
