# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_RJS_Semi_Naph_0m
_database_code_depnum_ccdc_archive 'CCDC 1908533'
loop_
_audit_author_name
_audit_author_address
'Rupam Jyoti sarma'
;Department of Chemistry Gauhati University
India
;
_audit_update_record             
;
2019-04-08 deposited with the CCDC.	2019-07-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H15 N3 O3'
_chemical_formula_sum            'C13 H15 N3 O3'
_chemical_formula_weight         261.28

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   10.2378(11)
_cell_length_b                   10.1117(9)
_cell_length_c                   13.0302(10)
_cell_angle_alpha                90
_cell_angle_beta                 92.895(5)
_cell_angle_gamma                90
_cell_volume                     1347.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3848
_cell_measurement_theta_min      2.47
_cell_measurement_theta_max      24.27

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_F_000             552
_exptl_transmission_factor_min   0.982
_exptl_transmission_factor_max   0.989
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.094
_shelx_estimated_absorpt_T_min   0.983
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'Sheldrick - 2016'
_exptl_absorpt_special_details   'Bruker AXS SADABS program'
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11012
_diffrn_reflns_av_unetI/netI     0.0258
_diffrn_reflns_av_R_equivalents  0.0270
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.131
_diffrn_reflns_theta_max         26.393
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             2740
_reflns_number_gt                2125
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0895P)²+0.1155P] 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         2740
_refine_ls_number_parameters     193
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0588
_refine_ls_R_factor_gt           0.0436
_refine_ls_wR_factor_ref         0.1450
_refine_ls_wR_factor_gt          0.1258
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_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 0.64475(13) 0.98525(14) 0.93077(10) 0.0370(3) Uani 1 1 d . . . . .
C2 C 0.68713(14) 1.05863(14) 1.01654(11) 0.0421(4) Uani 1 1 d . . . . .
C3 C 0.70630(16) 1.19667(16) 1.01077(14) 0.0548(4) Uani 1 1 d . . . . .
H3 H 0.734478 1.243565 1.069162 0.066 Uiso 1 1 calc R U . . .
C4 C 0.68383(17) 1.26079(16) 0.92068(15) 0.0596(5) Uani 1 1 d . . . . .
H4 H 0.696919 1.351714 0.917989 0.072 Uiso 1 1 calc R U . . .
C5 C 0.64093(15) 1.19293(17) 0.83054(13) 0.0534(4) Uani 1 1 d . . . . .
C6 C 0.6183(2) 1.2602(2) 0.73647(19) 0.0784(6) Uani 1 1 d . . . . .
H6 H 0.631872 1.350998 0.733662 0.094 Uiso 1 1 calc R U . . .
C7 C 0.5773(3) 1.1948(3) 0.65047(19) 0.0971(8) Uani 1 1 d . . . . .
H7 H 0.563331 1.240527 0.588983 0.117 Uiso 1 1 calc R U . . .
C8 C 0.5559(3) 1.0581(3) 0.65373(16) 0.0938(8) Uani 1 1 d . . . . .
H8 H 0.527223 1.013786 0.594247 0.113 Uiso 1 1 calc R U . . .
C9 C 0.5767(2) 0.9888(2) 0.74352(13) 0.0654(5) Uani 1 1 d . . . . .
H9 H 0.561967 0.898077 0.744257 0.079 Uiso 1 1 calc R U . . .
C10 C 0.62019(14) 1.05371(16) 0.83480(11) 0.0445(4) Uani 1 1 d . . . . .
C11 C 0.61875(13) 0.84435(14) 0.93924(10) 0.0373(3) Uani 1 1 d . . . . .
H11 H 0.577508 0.800300 0.883958 0.045 Uiso 1 1 calc R U . . .
C12 C 0.63651(15) 0.57627(14) 1.11119(10) 0.0408(3) Uani 1 1 d . . . . .
C13 C 0.5024(2) 0.6197(3) 0.6409(2) 0.0929(8) Uani 1 1 d . . . . .
H13A H 0.510503 0.675901 0.582165 0.139 Uiso 1 1 calc R U . . .
H13B H 0.466130 0.536104 0.619048 0.139 Uiso 1 1 calc R U . . .
H13C H 0.587055 0.605934 0.674188 0.139 Uiso 1 1 calc R U . . .
H1A H 0.701(2) 0.915(3) 1.1067(19) 0.097(8) Uiso 1 1 d . . . . .
H2A H 0.5565(17) 0.6176(16) 0.9799(13) 0.049(4) Uiso 1 1 d . . . . .
H3A H 0.7340(18) 0.5729(18) 1.2425(14) 0.057(5) Uiso 1 1 d . . . . .
H3B H 0.770(2) 0.697(2) 1.1741(14) 0.068(6) Uiso 1 1 d . . . . .
H3C H 0.417(2) 0.632(2) 0.7639(17) 0.075(6) Uiso 1 1 d . . . . .
N1 N 0.65136(11) 0.77936(11) 1.02120(8) 0.0379(3) Uani 1 1 d . . . . .
N2 N 0.61450(13) 0.64872(11) 1.02403(9) 0.0421(3) Uani 1 1 d . . . . .
N3 N 0.71882(15) 0.62361(15) 1.18412(11) 0.0584(4) Uani 1 1 d . . . . .
O1 O 0.70974(13) 1.00367(12) 1.11055(8) 0.0550(3) Uani 1 1 d . . . . .
O2 O 0.57920(12) 0.46817(10) 1.11830(8) 0.0553(3) Uani 1 1 d . . . . .
O3 O 0.41965(13) 0.67966(12) 0.70980(10) 0.0638(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
C1 C2 1.392(2) . ?
C1 C10 1.4403(19) . ?
C1 C11 1.455(2) . ?
C2 O1 1.3543(18) . ?
C2 C3 1.412(2) . ?
C3 C4 1.351(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.411(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.410(3) . ?
C5 C10 1.425(2) . ?
C6 C7 1.350(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.400(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.371(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.411(2) . ?
C9 H9 0.9300 . ?
C11 N1 1.2837(17) . ?
C11 H11 0.9300 . ?
C12 O2 1.2461(18) . ?
C12 N3 1.3272(19) . ?
C12 N2 1.3607(18) . ?
C13 O3 1.403(3) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
N1 N2 1.3748(16) . ?
N2 H2A 0.865(18) . ?
N3 H3A 0.925(19) . ?
N3 H3B 0.93(2) . ?
O1 H1A 0.91(3) . ?
O3 H3C 0.86(2) . ?

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 118.32(13) . . ?
C2 C1 C11 120.79(12) . . ?
C10 C1 C11 120.80(12) . . ?
O1 C2 C1 122.64(13) . . ?
O1 C2 C3 115.85(13) . . ?
C1 C2 C3 121.50(14) . . ?
C4 C3 C2 120.19(15) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C5 121.48(15) . . ?
C3 C4 H4 119.3 . . ?
C5 C4 H4 119.3 . . ?
C6 C5 C4 121.30(17) . . ?
C6 C5 C10 119.45(18) . . ?
C4 C5 C10 119.25(14) . . ?
C7 C6 C5 121.1(2) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C6 C7 C8 120.06(18) . . ?
C6 C7 H7 120.0 . . ?
C8 C7 H7 120.0 . . ?
C9 C8 C7 120.8(2) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C8 C9 C10 120.70(19) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
C9 C10 C5 117.90(14) . . ?
C9 C10 C1 122.84(14) . . ?
C5 C10 C1 119.26(14) . . ?
N1 C11 C1 121.58(12) . . ?
N1 C11 H11 119.2 . . ?
C1 C11 H11 119.2 . . ?
O2 C12 N3 123.20(13) . . ?
O2 C12 N2 118.39(12) . . ?
N3 C12 N2 118.41(14) . . ?
O3 C13 H13A 109.5 . . ?
O3 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O3 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 N1 N2 117.00(11) . . ?
C12 N2 N1 120.37(11) . . ?
C12 N2 H2A 116.0(11) . . ?
N1 N2 H2A 120.8(11) . . ?
C12 N3 H3A 117.6(11) . . ?
C12 N3 H3B 122.3(12) . . ?
H3A N3 H3B 119.3(17) . . ?
C2 O1 H1A 110.2(16) . . ?
C13 O3 H3C 108.9(14) . . ?

_refine_diff_density_max         0.178
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.059

####################################################################### 
# 
# 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_mono
_database_code_depnum_ccdc_archive 'CCDC 1908534'
loop_
_audit_author_name
_audit_author_address
'Rupam Jyoti sarma'
;Department of Chemistry Gauhati University
India
;
_audit_update_record             
;
2019-04-08 deposited with the CCDC.	2019-07-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H11 N3 O2'
_chemical_formula_weight         229.24

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/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                   16.1385(17)
_cell_length_b                   4.7309(5)
_cell_length_c                   15.7978(17)
_cell_angle_alpha                90
_cell_angle_beta                 114.296(5)
_cell_angle_gamma                90
_cell_volume                     1099.3(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4205
_cell_measurement_theta_min      2.59
_cell_measurement_theta_max      28.60

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_F_000             480
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.098
_shelx_estimated_absorpt_T_min   0.980
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.979
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_process_details   'Bruker AXS SADABS program'
_exptl_absorpt_special_details   Sheldrick,G.M.,(2003)
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10447
_diffrn_reflns_av_unetI/netI     0.0817
_diffrn_reflns_av_R_equivalents  0.1340
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.384
_diffrn_reflns_theta_max         29.100
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2915
_reflns_number_gt                2046
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0886P)²+0.0258P] 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     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.055(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2915
_refine_ls_number_parameters     171
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0893
_refine_ls_R_factor_gt           0.0602
_refine_ls_wR_factor_ref         0.1743
_refine_ls_wR_factor_gt          0.1476
_refine_ls_goodness_of_fit_ref   1.125
_refine_ls_restrained_S_all      1.125
_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
C1 C 0.73737(8) 0.2920(3) 0.65399(9) 0.0302(3) Uani 1 1 d . . . . .
C2 C 0.74264(9) 0.3887(3) 0.73949(10) 0.0377(4) Uani 1 1 d . . . . .
C3 C 0.80738(11) 0.5906(3) 0.79144(11) 0.0469(4) Uani 1 1 d . . . . .
H3 H 0.809843 0.650003 0.848546 0.056 Uiso 1 1 calc R U . . .
C4 C 0.86634(10) 0.6994(3) 0.75882(11) 0.0462(4) Uani 1 1 d . . . . .
H4 H 0.908961 0.832576 0.794040 0.055 Uiso 1 1 calc R U . . .
C5 C 0.86409(9) 0.6134(3) 0.67187(10) 0.0377(4) Uani 1 1 d . . . . .
C6 C 0.92509(10) 0.7284(4) 0.63695(13) 0.0504(5) Uani 1 1 d . . . . .
H6 H 0.967530 0.862595 0.671782 0.060 Uiso 1 1 calc R U . . .
C7 C 0.92256(11) 0.6456(4) 0.55338(14) 0.0550(5) Uani 1 1 d . . . . .
H7 H 0.963362 0.722015 0.531818 0.066 Uiso 1 1 calc R U . . .
C8 C 0.85885(12) 0.4466(4) 0.50023(13) 0.0504(4) Uani 1 1 d . . . . .
H8 H 0.857198 0.391143 0.443085 0.061 Uiso 1 1 calc R U . . .
C9 C 0.79837(10) 0.3314(3) 0.53148(10) 0.0407(4) Uani 1 1 d . . . . .
H9 H 0.755888 0.200370 0.494644 0.049 Uiso 1 1 calc R U . . .
C10 C 0.79935(8) 0.4080(3) 0.61851(9) 0.0312(3) Uani 1 1 d . . . . .
C11 C 0.67322(9) 0.0705(3) 0.60419(9) 0.0312(3) Uani 1 1 d . . . . .
H11 H 0.677659 -0.018077 0.553677 0.037 Uiso 1 1 calc R U . . .
C12 C 0.48054(9) -0.2846(3) 0.60299(10) 0.0341(3) Uani 1 1 d . . . . .
H1A H 0.6521(16) 0.162(5) 0.7402(17) 0.079(7) Uiso 1 1 d . . . . .
H2A H 0.5645(11) -0.316(3) 0.5441(13) 0.042(4) Uiso 1 1 d . . . . .
H3A H 0.4784(13) 0.068(5) 0.6603(13) 0.060(6) Uiso 1 1 d . . . . .
H3B H 0.4098(12) -0.129(3) 0.6621(12) 0.047(5) Uiso 1 1 d . . . . .
N1 N 0.61038(8) -0.0027(2) 0.62998(8) 0.0357(3) Uani 1 1 d . . . . .
N2 N 0.55516(8) -0.2251(3) 0.58613(9) 0.0386(3) Uani 1 1 d . . . . .
N3 N 0.45978(10) -0.1016(3) 0.65602(11) 0.0483(4) Uani 1 1 d . . . . .
O1 O 0.68683(9) 0.2913(3) 0.77804(9) 0.0540(4) Uani 1 1 d . . . . .
O2 O 0.43646(7) -0.5020(2) 0.57073(8) 0.0446(3) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.3952(19) . ?
C1 C10 1.4413(18) . ?
C1 C11 1.4553(18) . ?
C2 O1 1.3586(18) . ?
C2 C3 1.404(2) . ?
C3 C4 1.356(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.419(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.420(2) . ?
C5 C10 1.4219(19) . ?
C6 C7 1.361(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.392(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.375(2) . ?
C8 H8 0.9300 . ?
C9 C10 1.416(2) . ?
C9 H9 0.9300 . ?
C11 N1 1.2862(16) . ?
C11 H11 0.9300 . ?
C12 O2 1.2352(16) . ?
C12 N3 1.3395(19) . ?
C12 N2 1.3655(17) . ?
N1 N2 1.3684(16) . ?
N2 H2A 0.854(19) . ?
N3 H3A 0.85(2) . ?
N3 H3B 0.861(18) . ?
O1 H1A 0.88(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C10 118.42(12) . . ?
C2 C1 C11 120.39(12) . . ?
C10 C1 C11 121.14(12) . . ?
O1 C2 C1 122.34(13) . . ?
O1 C2 C3 116.10(13) . . ?
C1 C2 C3 121.55(13) . . ?
C4 C3 C2 120.37(15) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 121.11(14) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 H4 119.4 . . ?
C4 C5 C6 121.38(15) . . ?
C4 C5 C10 119.32(13) . . ?
C6 C5 C10 119.30(14) . . ?
C7 C6 C5 121.17(16) . . ?
C7 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
C6 C7 C8 119.96(14) . . ?
C6 C7 H7 120.0 . . ?
C8 C7 H7 120.0 . . ?
C9 C8 C7 120.58(16) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C8 C9 C10 121.43(15) . . ?
C8 C9 H9 119.3 . . ?
C10 C9 H9 119.3 . . ?
C9 C10 C5 117.55(12) . . ?
C9 C10 C1 123.23(13) . . ?
C5 C10 C1 119.21(13) . . ?
N1 C11 C1 120.07(12) . . ?
N1 C11 H11 120.0 . . ?
C1 C11 H11 120.0 . . ?
O2 C12 N3 123.12(13) . . ?
O2 C12 N2 119.71(13) . . ?
N3 C12 N2 117.16(13) . . ?
C11 N1 N2 118.74(12) . . ?
C12 N2 N1 120.17(13) . . ?
C12 N2 H2A 120.0(11) . . ?
N1 N2 H2A 119.5(11) . . ?
C12 N3 H3A 119.3(13) . . ?
C12 N3 H3B 117.2(11) . . ?
H3A N3 H3B 116.9(17) . . ?
C2 O1 H1A 106.6(15) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C10 C1 C2 O1 179.90(12) . . . . ?
C11 C1 C2 O1 -2.7(2) . . . . ?
C10 C1 C2 C3 -1.1(2) . . . . ?
C11 C1 C2 C3 176.35(14) . . . . ?
O1 C2 C3 C4 179.73(14) . . . . ?
C1 C2 C3 C4 0.7(2) . . . . ?
C2 C3 C4 C5 0.2(3) . . . . ?
C3 C4 C5 C6 179.43(14) . . . . ?
C3 C4 C5 C10 -0.5(2) . . . . ?
C4 C5 C6 C7 -179.87(15) . . . . ?
C10 C5 C6 C7 0.1(2) . . . . ?
C5 C6 C7 C8 0.5(3) . . . . ?
C6 C7 C8 C9 -0.2(3) . . . . ?
C7 C8 C9 C10 -0.7(2) . . . . ?
C8 C9 C10 C5 1.3(2) . . . . ?
C8 C9 C10 C1 -179.84(13) . . . . ?
C4 C5 C10 C9 178.99(12) . . . . ?
C6 C5 C10 C9 -0.94(19) . . . . ?
C4 C5 C10 C1 0.1(2) . . . . ?
C6 C5 C10 C1 -179.88(12) . . . . ?
C2 C1 C10 C9 -178.15(12) . . . . ?
C11 C1 C10 C9 4.4(2) . . . . ?
C2 C1 C10 C5 0.7(2) . . . . ?
C11 C1 C10 C5 -176.70(11) . . . . ?
C2 C1 C11 N1 12.2(2) . . . . ?
C10 C1 C11 N1 -170.44(12) . . . . ?
C1 C11 N1 N2 -175.37(11) . . . . ?
O2 C12 N2 N1 -172.55(12) . . . . ?
N3 C12 N2 N1 6.4(2) . . . . ?
C11 N1 N2 C12 -171.27(12) . . . . ?

_refine_diff_density_max         0.446
_refine_diff_density_min         -0.360
_refine_diff_density_rms         0.146

