# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_Mother
_database_code_depnum_ccdc_archive 'CCDC 2069188'
loop_
_audit_author_name
_audit_author_address
'Toshiyuki Sasaki'
;Yokohama City University
Japan
;
_audit_update_record             
;
2021-03-10 deposited with the CCDC.	2021-04-05 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT084_Mother              
;
PROBLEM: High wR2 Value (i.e. > 0.25) ...................       0.48 Report
RESPONSE: The crystal was mechanically twinned.
;
_vrf_PLAT082_Mother              
;
PROBLEM: High R1 Value ..................................       0.18 Report
RESPONSE: The crystal was mechanically twinned.
;
_vrf_PLAT097_Mother              
;
PROBLEM: Large Reported Max.  (Positive) Residual Density       1.33 eA-3
RESPONSE: The crystal was mechanically twinned.
;
# Added during the CSD deposition process: Wednesday 10 March 2021 04:54 AM
# end Validation Reply Form


_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        7-Amino-4-methylcoumarin
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H9 N O2'
_chemical_formula_weight         175.18

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'
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                   6.9349(19)
_cell_length_b                   7.1467(15)
_cell_length_c                   9.558(2)
_cell_angle_alpha                71.817(6)
_cell_angle_beta                 84.968(8)
_cell_angle_gamma                70.026(8)
_cell_volume                     422.89(18)
_cell_formula_units_Z            2
_cell_measurement_temperature    296
_cell_measurement_reflns_used    620
_cell_measurement_theta_min      2.2435
_cell_measurement_theta_max      21.245

_exptl_crystal_description       platelet
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_F_000             184
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.245
_exptl_crystal_size_mid          0.124
_exptl_crystal_size_min          0.099
_exptl_absorpt_coefficient_mu    0.097
_shelx_estimated_absorpt_T_min   0.980
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6046
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro focus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 goniometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5217
_diffrn_reflns_av_unetI/netI     0.0614
_diffrn_reflns_av_R_equivalents  0.0610
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.243
_diffrn_reflns_theta_max         25.019
_diffrn_reflns_theta_full        25.019
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measured_fraction_theta_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_point_group_measured_fraction_full 0.977
_reflns_number_total             1468
_reflns_number_gt                862
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       
'Bruker Instrument Service V6.2.14 (Bruker AXS Inc., 2016)'
_computing_cell_refinement       'APEX3 v2019.11 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.2000P)²] 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         1468
_refine_ls_number_parameters     119
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2083
_refine_ls_R_factor_gt           0.1819
_refine_ls_wR_factor_ref         0.4751
_refine_ls_wR_factor_gt          0.4492
_refine_ls_goodness_of_fit_ref   1.653
_refine_ls_restrained_S_all      1.653
_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 0.1448(6) 0.7230(6) 0.6587(4) 0.0536(14) Uani 1 1 d . . . . .
C3 C 0.3020(9) 0.2883(8) 0.7245(6) 0.0476(16) Uani 1 1 d . . . . .
C6 C 0.2038(9) 0.7009(9) 0.2845(6) 0.0475(16) Uani 1 1 d . . . . .
O2 O 0.1114(8) 0.6980(7) 0.8932(4) 0.0764(18) Uani 1 1 d . . . . .
C8 C 0.1956(8) 0.6355(8) 0.5455(5) 0.0418(15) Uani 1 1 d . . . . .
C4 C 0.3135(10) 0.3481(9) 0.4496(6) 0.0524(17) Uani 1 1 d . . . . .
H4 H 0.364491 0.205096 0.463086 0.063 Uiso 1 1 calc R U . . .
C2 C 0.2491(10) 0.3810(9) 0.8316(6) 0.0541(17) Uani 1 1 d . . . . .
H2 H 0.267610 0.296698 0.929074 0.065 Uiso 1 1 calc R U . . .
C9 C 0.2728(9) 0.4197(8) 0.5738(6) 0.0444(16) Uani 1 1 d . . . . .
C7 C 0.1608(9) 0.7733(8) 0.4069(6) 0.0481(16) Uani 1 1 d . . . . .
H7 H 0.108117 0.916023 0.394157 0.058 Uiso 1 1 calc R U . . .
C5 C 0.2807(10) 0.4817(9) 0.3100(6) 0.0546(18) Uani 1 1 d . . . . .
H5 H 0.308989 0.428589 0.230349 0.066 Uiso 1 1 calc R U . . .
N1 N 0.1718(9) 0.8353(9) 0.1450(5) 0.0667(18) Uani 1 1 d . . . . .
H1A H 0.124076 0.967827 0.131302 0.080 Uiso 1 1 calc R U . . .
H1B H 0.199277 0.787631 0.070748 0.080 Uiso 1 1 calc R U . . .
C1 C 0.1661(11) 0.6016(10) 0.8033(6) 0.0560(18) Uani 1 1 d . . . . .
C10 C 0.3877(12) 0.0559(9) 0.7605(7) 0.066(2) Uani 1 1 d . . . . .
H10A H 0.385321 -0.006338 0.865065 0.099 Uiso 1 1 calc R U . . .
H10B H 0.526570 0.016028 0.727773 0.099 Uiso 1 1 calc R U . . .
H10C H 0.306349 0.008825 0.711841 0.099 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.372(7) . ?
O1 C8 1.375(6) . ?
C3 C2 1.347(8) . ?
C3 C9 1.440(7) . ?
C3 C10 1.495(8) . ?
C6 N1 1.362(7) . ?
C6 C7 1.391(8) . ?
C6 C5 1.419(8) . ?
O2 C1 1.221(7) . ?
C8 C7 1.365(7) . ?
C8 C9 1.392(8) . ?
C4 C5 1.361(8) . ?
C4 C9 1.405(8) . ?
C4 H4 0.9300 . ?
C2 C1 1.426(9) . ?
C2 H2 0.9300 . ?
C7 H7 0.9300 . ?
C5 H5 0.9300 . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 C8 121.5(4) . . ?
C2 C3 C9 118.0(5) . . ?
C2 C3 C10 121.1(5) . . ?
C9 C3 C10 120.9(5) . . ?
N1 C6 C7 121.3(5) . . ?
N1 C6 C5 121.0(5) . . ?
C7 C6 C5 117.6(5) . . ?
C7 C8 O1 115.6(5) . . ?
C7 C8 C9 123.4(5) . . ?
O1 C8 C9 121.0(5) . . ?
C5 C4 C9 122.0(5) . . ?
C5 C4 H4 119.0 . . ?
C9 C4 H4 119.0 . . ?
C3 C2 C1 123.4(5) . . ?
C3 C2 H2 118.3 . . ?
C1 C2 H2 118.3 . . ?
C8 C9 C4 116.0(5) . . ?
C8 C9 C3 118.9(5) . . ?
C4 C9 C3 125.2(5) . . ?
C8 C7 C6 120.2(5) . . ?
C8 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
C4 C5 C6 120.8(5) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C6 N1 H1A 120.0 . . ?
C6 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
O2 C1 O1 115.1(5) . . ?
O2 C1 C2 127.6(6) . . ?
O1 C1 C2 117.3(5) . . ?
C3 C10 H10A 109.5 . . ?
C3 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C3 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?

_refine_diff_density_max         1.328
_refine_diff_density_min         -0.538
_refine_diff_density_rms         0.268


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetone'
####################################################################### 
# 
# 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_Daughter
_database_code_depnum_ccdc_archive 'CCDC 2069189'
loop_
_audit_author_name
_audit_author_address
'Toshiyuki Sasaki'
;Yokohama City University
Japan
;
_audit_update_record             
;
2021-03-10 deposited with the CCDC.	2021-04-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        7-Amino-4-methylcoumarin
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H9 N O2'
_chemical_formula_weight         175.18

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'
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                   6.9361(7)
_cell_length_b                   7.1569(6)
_cell_length_c                   9.5654(9)
_cell_angle_alpha                71.825(3)
_cell_angle_beta                 84.915(3)
_cell_angle_gamma                69.902(3)
_cell_volume                     423.58(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    296
_cell_measurement_reflns_used    991
_cell_measurement_theta_min      2.2415
_cell_measurement_theta_max      24.948

_exptl_crystal_description       platelet
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_F_000             184
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.171
_exptl_crystal_size_mid          0.115
_exptl_crystal_size_min          0.082
_exptl_absorpt_coefficient_mu    0.097
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6549
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro focus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 goniometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5247
_diffrn_reflns_av_unetI/netI     0.0424
_diffrn_reflns_av_R_equivalents  0.0449
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.241
_diffrn_reflns_theta_max         25.013
_diffrn_reflns_theta_full        25.013
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measured_fraction_theta_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_point_group_measured_fraction_full 0.978
_reflns_number_total             1473
_reflns_number_gt                1044
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       
'Bruker Instrument Service V6.2.14 (Bruker AXS Inc., 2016)'
_computing_cell_refinement       'APEX3 v2019.11 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.1148P)²+0.0358P] 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         1473
_refine_ls_number_parameters     119
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0803
_refine_ls_R_factor_gt           0.0632
_refine_ls_wR_factor_ref         0.1973
_refine_ls_wR_factor_gt          0.1731
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_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 0.6455(2) 0.7217(2) 0.65903(15) 0.0481(5) Uani 1 1 d . . . . .
O2 O 0.6105(3) 0.6965(3) 0.89318(17) 0.0718(7) Uani 1 1 d . . . . .
N1 N 0.6721(3) 0.8350(3) 0.14516(19) 0.0596(7) Uani 1 1 d . . . . .
H1A H 0.626347 0.967387 0.131729 0.071 Uiso 1 1 calc R U . . .
H1B H 0.698388 0.787684 0.070743 0.071 Uiso 1 1 calc R U . . .
C9 C 0.7721(3) 0.4193(3) 0.5733(2) 0.0399(6) Uani 1 1 d . . . . .
C8 C 0.6948(3) 0.6346(3) 0.5452(2) 0.0400(6) Uani 1 1 d . . . . .
C6 C 0.7028(3) 0.7003(4) 0.2843(2) 0.0449(6) Uani 1 1 d . . . . .
C3 C 0.8021(3) 0.2884(3) 0.7248(2) 0.0434(6) Uani 1 1 d . . . . .
C2 C 0.7488(4) 0.3804(4) 0.8322(2) 0.0496(6) Uani 1 1 d . . . . .
H2 H 0.766376 0.296382 0.929628 0.060 Uiso 1 1 calc R U . . .
C5 C 0.7808(3) 0.4833(3) 0.3095(2) 0.0489(6) Uani 1 1 d . . . . .
H5 H 0.810459 0.430569 0.229738 0.059 Uiso 1 1 calc R U . . .
C7 C 0.6612(3) 0.7736(3) 0.4062(2) 0.0437(6) Uani 1 1 d . . . . .
H7 H 0.610710 0.916287 0.393474 0.052 Uiso 1 1 calc R U . . .
C4 C 0.8139(3) 0.3484(4) 0.4493(2) 0.0480(6) Uani 1 1 d . . . . .
H4 H 0.865668 0.205581 0.462422 0.058 Uiso 1 1 calc R U . . .
C1 C 0.6665(4) 0.6010(4) 0.8030(2) 0.0501(6) Uani 1 1 d . . . . .
C10 C 0.8882(4) 0.0568(3) 0.7606(3) 0.0583(7) Uani 1 1 d . . . . .
H10A H 0.890971 -0.005183 0.865383 0.087 Uiso 1 1 calc R U . . .
H10B H 1.025270 0.017379 0.724384 0.087 Uiso 1 1 calc R U . . .
H10C H 0.803896 0.009207 0.715208 0.087 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.368(3) . ?
O1 C8 1.379(2) . ?
O2 C1 1.220(3) . ?
N1 C6 1.362(3) . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
C9 C8 1.390(3) . ?
C9 C4 1.401(3) . ?
C9 C3 1.447(3) . ?
C8 C7 1.372(3) . ?
C6 C7 1.391(3) . ?
C6 C5 1.405(3) . ?
C3 C2 1.347(3) . ?
C3 C10 1.491(3) . ?
C2 C1 1.425(3) . ?
C2 H2 0.9300 . ?
C5 C4 1.368(3) . ?
C5 H5 0.9300 . ?
C7 H7 0.9300 . ?
C4 H4 0.9300 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 C8 121.69(17) . . ?
C6 N1 H1A 120.0 . . ?
C6 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
C8 C9 C4 115.88(19) . . ?
C8 C9 C3 118.54(18) . . ?
C4 C9 C3 125.59(19) . . ?
C7 C8 O1 115.61(18) . . ?
C7 C8 C9 123.57(19) . . ?
O1 C8 C9 120.82(18) . . ?
N1 C6 C7 120.9(2) . . ?
N1 C6 C5 121.20(19) . . ?
C7 C6 C5 117.89(19) . . ?
C2 C3 C9 118.50(19) . . ?
C2 C3 C10 120.9(2) . . ?
C9 C3 C10 120.58(19) . . ?
C3 C2 C1 122.8(2) . . ?
C3 C2 H2 118.6 . . ?
C1 C2 H2 118.6 . . ?
C4 C5 C6 121.09(19) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C8 C7 C6 119.76(19) . . ?
C8 C7 H7 120.1 . . ?
C6 C7 H7 120.1 . . ?
C5 C4 C9 121.82(19) . . ?
C5 C4 H4 119.1 . . ?
C9 C4 H4 119.1 . . ?
O2 C1 O1 115.4(2) . . ?
O2 C1 C2 127.0(2) . . ?
O1 C1 C2 117.61(19) . . ?
C3 C10 H10A 109.5 . . ?
C3 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C3 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?

_refine_diff_density_max         0.281
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.062





_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetone'
