# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2144927'
loop_
_audit_author_name
_audit_author_address
'Subhra Kanti Roy'
;Indian Institute of Technology, Guwahati
India
;
_audit_update_record             
;
2022-01-27 deposited with the CCDC.	2022-04-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        2-(pyrrolidin-1-yl)naphtho[1,2-d]oxazole
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H14 N2 O'
_chemical_compound_source        synthesis
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethyl acetate and hexane'
_chemical_melting_point          ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless

_diffrn_ambient_temperature      293(2)
_chemical_formula_weight         238.28

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/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                   6.3429(12)
_cell_length_b                   15.1467(18)
_cell_length_c                   12.9960(16)
_cell_angle_alpha                90
_cell_angle_beta                 103.927(17)
_cell_angle_gamma                90
_cell_volume                     1211.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3297
_cell_measurement_theta_min      3.23
_cell_measurement_theta_max      24.997
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_F_000             504
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.35
_exptl_absorpt_coefficient_mu    0.083
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.967
_exptl_absorpt_correction_T_max  0.971
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3001
_diffrn_reflns_av_unetI/netI     0.0480
_diffrn_reflns_av_R_equivalents  0.0317
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.230
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.845
_diffrn_measured_fraction_theta_full 0.822
_diffrn_reflns_Laue_measured_fraction_max 0.845
_diffrn_reflns_Laue_measured_fraction_full 0.822
_diffrn_reflns_point_group_measured_fraction_max 0.845
_diffrn_reflns_point_group_measured_fraction_full 0.822
_reflns_number_total             1806
_reflns_number_gt                1284
_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'
_computing_cell_refinement       'CrysAlisPro, Agilent Technologies'
_computing_data_reduction        'CrysAlisPro, Agilent Technologies'
_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)+(0.1153P)²+0.3098P] 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         1806
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0969
_refine_ls_R_factor_gt           0.0746
_refine_ls_wR_factor_ref         0.2267
_refine_ls_wR_factor_gt          0.1996
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_restrained_S_all      1.096
_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 -0.1551(4) 0.41592(15) 0.03272(17) 0.0551(7) Uani 1 1 d . . . . .
N2 N 0.1515(5) 0.39120(17) 0.16327(18) 0.0477(8) Uani 1 1 d . . . . .
N1 N -0.1308(5) 0.48232(19) 0.1941(2) 0.0585(9) Uani 1 1 d . . . . .
C11 C 0.3225(6) 0.28580(19) 0.0533(2) 0.0439(9) Uani 1 1 d . . . . .
C5 C -0.0380(6) 0.4306(2) 0.1355(2) 0.0503(9) Uani 1 1 d . . . . .
C10 C 0.2792(6) 0.2430(2) -0.0469(2) 0.0484(9) Uani 1 1 d . . . . .
C6 C 0.1615(6) 0.34320(19) 0.0720(2) 0.0449(9) Uani 1 1 d . . . . .
C13 C 0.6712(6) 0.2129(2) 0.1031(3) 0.0596(10) Uani 1 1 d . . . . .
H13 H 0.8025 0.2033 0.1521 0.072 Uiso 1 1 calc R U . . .
C7 C -0.0238(6) 0.3579(2) -0.0062(3) 0.0504(9) Uani 1 1 d . . . . .
C9 C 0.0826(6) 0.2601(2) -0.1241(3) 0.0587(11) Uani 1 1 d . . . . .
H9 H 0.0573 0.2313 -0.1892 0.070 Uiso 1 1 calc R U . . .
C4 C -0.3497(6) 0.5194(2) 0.1598(3) 0.0631(11) Uani 1 1 d . . . . .
H4A H -0.4528 0.4754 0.1241 0.076 Uiso 1 1 calc R U . . .
H4B H -0.3523 0.5694 0.1129 0.076 Uiso 1 1 calc R U . . .
C12 C 0.5223(6) 0.2692(2) 0.1274(2) 0.0498(9) Uani 1 1 d . . . . .
H12 H 0.5521 0.2969 0.1932 0.060 Uiso 1 1 calc R U . . .
C14 C 0.6281(7) 0.1694(2) 0.0047(3) 0.0631(11) Uani 1 1 d . . . . .
H14 H 0.7297 0.1305 -0.0108 0.076 Uiso 1 1 calc R U . . .
C1 C -0.0314(7) 0.4988(2) 0.3054(3) 0.0664(11) Uani 1 1 d . . . . .
H1A H 0.1054 0.5298 0.3136 0.080 Uiso 1 1 calc R U . . .
H1B H -0.0055 0.4439 0.3447 0.080 Uiso 1 1 calc R U . . .
C2 C -0.1923(8) 0.5543(3) 0.3426(4) 0.0898(15) Uani 1 1 d . . . . .
H2A H -0.2096 0.5333 0.4106 0.108 Uiso 1 1 calc R U . . .
H2B H -0.1441 0.6153 0.3504 0.108 Uiso 1 1 calc R U . . .
C8 C -0.0702(7) 0.3177(2) -0.1053(3) 0.0621(11) Uani 1 1 d . . . . .
H8 H -0.1980 0.3293 -0.1560 0.074 Uiso 1 1 calc R U . . .
C15 C 0.4366(7) 0.1843(2) -0.0680(3) 0.0585(11) Uani 1 1 d . . . . .
H15 H 0.4094 0.1552 -0.1329 0.070 Uiso 1 1 calc R U . . .
C3 C -0.3974(8) 0.5474(4) 0.2627(4) 0.116(2) Uani 1 1 d . . . . .
H3A H -0.4713 0.6040 0.2541 0.139 Uiso 1 1 calc R U . . .
H3B H -0.4909 0.5043 0.2847 0.139 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 C5 1.381(4) . ?
O1 C7 1.387(4) . ?
N2 C5 1.312(4) . ?
N2 C6 1.406(4) . ?
N1 C5 1.325(4) . ?
N1 C1 1.453(4) . ?
N1 C4 1.465(4) . ?
C11 C6 1.407(4) . ?
C11 C12 1.418(5) . ?
C11 C10 1.421(4) . ?
C10 C15 1.412(5) . ?
C10 C9 1.423(5) . ?
C6 C7 1.374(5) . ?
C13 C12 1.364(5) . ?
C13 C14 1.406(5) . ?
C7 C8 1.391(4) . ?
C9 C8 1.369(5) . ?
C4 C3 1.502(6) . ?
C14 C15 1.367(5) . ?
C1 C2 1.490(5) . ?
C2 C3 1.460(6) . ?

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
C5 O1 C7 103.0(2) . . ?
C5 N2 C6 103.1(3) . . ?
C5 N1 C1 121.8(3) . . ?
C5 N1 C4 124.8(3) . . ?
C1 N1 C4 112.9(3) . . ?
C6 C11 C12 124.0(3) . . ?
C6 C11 C10 116.9(3) . . ?
C12 C11 C10 119.1(3) . . ?
N2 C5 N1 127.9(3) . . ?
N2 C5 O1 115.9(3) . . ?
N1 C5 O1 116.2(3) . . ?
C15 C10 C11 118.4(3) . . ?
C15 C10 C9 121.2(3) . . ?
C11 C10 C9 120.4(3) . . ?
C7 C6 C11 120.0(3) . . ?
C7 C6 N2 109.6(3) . . ?
C11 C6 N2 130.4(3) . . ?
C12 C13 C14 120.7(3) . . ?
C6 C7 O1 108.3(3) . . ?
C6 C7 C8 124.5(3) . . ?
O1 C7 C8 127.1(3) . . ?
C8 C9 C10 121.9(3) . . ?
N1 C4 C3 102.5(3) . . ?
C13 C12 C11 120.6(3) . . ?
C15 C14 C13 119.8(3) . . ?
N1 C1 C2 104.7(3) . . ?
C3 C2 C1 106.9(4) . . ?
C9 C8 C7 116.3(3) . . ?
C14 C15 C10 121.5(3) . . ?
C2 C3 C4 108.5(4) . . ?

_refine_diff_density_max         0.240
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.059

_shelxl_version_number           2013-4

_symmetry_cell_setting           ?
_symmetry_space_group_name_h-m   ?
_symmetry_int_tables_number      ?
_chemical_absolute_configuration ?

####################################################################### 
# 
# 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_exp_4018
_database_code_depnum_ccdc_archive 'CCDC 2144943'
loop_
_audit_author_name
_audit_author_address
'Subhra Kanti Roy' 'Indian Institute of Technology, Guwahati'
_audit_update_record             
;
2022-01-27 deposited with the CCDC.	2022-04-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        2-(azepan-1-yl)phenanthro[9,10-d]oxazole
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H20 N2 O'
_chemical_compound_source        synthesis
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethyl acetate and hexane'
_chemical_melting_point          ?

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow

_diffrn_ambient_temperature      293(2)
_chemical_formula_weight         316.39

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21'
_symmetry_int_tables_number      4
_chemical_absolute_configuration ?

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

_cell_length_a                   11.6978(6)
_cell_length_b                   5.1772(2)
_cell_length_c                   14.0219(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.748(6)
_cell_angle_gamma                90.00
_cell_volume                     808.78(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3420
_cell_measurement_theta_min      3.04
_cell_measurement_theta_max      25.00
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             336
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.972
_exptl_absorpt_correction_T_max  0.976
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            2991
_diffrn_reflns_av_R_equivalents  0.0115
_diffrn_reflns_av_sigmaI/netI    0.0280
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.04
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2239
_reflns_number_gt                1986
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0512P)²+0.1319P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.028(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -4(3)
_refine_ls_number_reflns         2239
_refine_ls_number_parameters     218
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0491
_refine_ls_R_factor_gt           0.0428
_refine_ls_wR_factor_ref         0.1205
_refine_ls_wR_factor_gt          0.1148
_refine_ls_goodness_of_fit_ref   1.199
_refine_ls_restrained_S_all      1.198
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.78518(18) 0.4174(4) 0.32534(16) 0.0361(5) Uani 1 1 d . . .
O1 O 0.60323(18) 0.4186(4) 0.20796(16) 0.0585(6) Uani 1 1 d . . .
N2 N 0.7479(2) 0.1244(5) 0.19081(18) 0.0498(6) Uani 1 1 d . . .
C1 C 0.7139(3) 0.3149(6) 0.2412(2) 0.0490(8) Uani 1 1 d . . .
C3 C 0.7149(2) 0.6044(5) 0.3503(2) 0.0424(7) Uani 1 1 d . . .
C16 C 0.6052(2) 0.6083(6) 0.2796(2) 0.0413(6) Uani 1 1 d . . .
C15 C 0.5131(2) 0.7830(6) 0.2818(2) 0.0440(7) Uani 1 1 d . . .
C9 C 0.6601(2) 0.9641(6) 0.4378(2) 0.0427(7) Uani 1 1 d . . .
C4 C 0.7480(2) 0.7821(6) 0.4323(2) 0.0433(7) Uani 1 1 d . . .
C10 C 0.5411(2) 0.9637(6) 0.3620(2) 0.0435(7) Uani 1 1 d . . .
C8 C 0.6921(3) 1.1413(6) 0.5175(2) 0.0544(8) Uani 1 1 d . . .
H8 H 0.6357 1.2612 0.5238 0.065 Uiso 1 1 calc R . .
C5 C 0.8629(3) 0.7832(7) 0.5041(2) 0.0510(8) Uani 1 1 d . . .
H5 H 0.9199 0.6616 0.5004 0.061 Uiso 1 1 calc R . .
C14 C 0.4000(3) 0.7842(7) 0.2100(2) 0.0550(8) Uani 1 1 d . . .
H14 H 0.3824 0.6634 0.1585 0.066 Uiso 1 1 calc R . .
C11 C 0.4499(3) 1.1418(6) 0.3638(2) 0.0543(8) Uani 1 1 d . . .
H11 H 0.4644 1.2618 0.4155 0.065 Uiso 1 1 calc R . .
C24 C 0.6625(3) 0.0313(7) 0.0977(2) 0.0570(8) Uani 1 1 d . . .
H24A H 0.6254 0.1789 0.0576 0.068 Uiso 1 1 calc R . .
H24B H 0.5997 -0.0650 0.1138 0.068 Uiso 1 1 calc R . .
C19 C 0.8657(3) 0.0061(7) 0.2347(2) 0.0537(8) Uani 1 1 d . . .
H19A H 0.8570 -0.1803 0.2302 0.064 Uiso 1 1 calc R . .
H19B H 0.8950 0.0514 0.3051 0.064 Uiso 1 1 calc R . .
C20 C 0.9574(3) 0.0875(7) 0.1848(2) 0.0597(9) Uani 1 1 d . . .
H20A H 1.0371 0.0534 0.2299 0.072 Uiso 1 1 calc R . .
H20B H 0.9506 0.2722 0.1727 0.072 Uiso 1 1 calc R . .
C12 C 0.3405(3) 1.1409(7) 0.2909(3) 0.0647(10) Uani 1 1 d . . .
H12 H 0.2830 1.2632 0.2929 0.078 Uiso 1 1 calc R . .
C7 C 0.8036(3) 1.1420(7) 0.5857(2) 0.0631(9) Uani 1 1 d . . .
H7 H 0.8224 1.2630 0.6372 0.076 Uiso 1 1 calc R . .
C6 C 0.8902(3) 0.9627(8) 0.5790(2) 0.0616(9) Uani 1 1 d . . .
H6 H 0.9663 0.9656 0.6255 0.074 Uiso 1 1 calc R . .
C23 C 0.7181(3) -0.1394(6) 0.0358(3) 0.0625(9) Uani 1 1 d . . .
H23A H 0.6562 -0.1877 -0.0252 0.075 Uiso 1 1 calc R . .
H23B H 0.7468 -0.2966 0.0731 0.075 Uiso 1 1 calc R . .
C13 C 0.3147(3) 0.9609(8) 0.2146(3) 0.0656(9) Uani 1 1 d . . .
H13 H 0.2396 0.9596 0.1666 0.079 Uiso 1 1 calc R . .
C21 C 0.9432(3) -0.0516(9) 0.0853(2) 0.0684(10) Uani 1 1 d . . .
H21A H 1.0049 0.0103 0.0578 0.082 Uiso 1 1 calc R . .
H21B H 0.9567 -0.2348 0.0986 0.082 Uiso 1 1 calc R . .
C22 C 0.8221(3) -0.0159(9) 0.0075(2) 0.0699(10) Uani 1 1 d . . .
H22A H 0.8250 -0.0897 -0.0553 0.084 Uiso 1 1 calc R . .
H22B H 0.8064 0.1675 -0.0031 0.084 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
N1 C1 1.330(4) . ?
N1 C3 1.382(3) . ?
O1 C1 1.347(4) . ?
O1 C16 1.400(3) . ?
N2 C1 1.342(4) . ?
N2 C19 1.461(4) . ?
N2 C24 1.463(4) . ?
C3 C16 1.362(4) . ?
C3 C4 1.430(4) . ?
C16 C15 1.414(4) . ?
C15 C14 1.397(4) . ?
C15 C10 1.423(4) . ?
C9 C8 1.406(4) . ?
C9 C4 1.415(4) . ?
C9 C10 1.471(4) . ?
C4 C5 1.412(4) . ?
C10 C11 1.416(4) . ?
C8 C7 1.362(4) . ?
C8 H8 0.9300 . ?
C5 C6 1.365(5) . ?
C5 H5 0.9300 . ?
C14 C13 1.370(5) . ?
C14 H14 0.9300 . ?
C11 C12 1.373(4) . ?
C11 H11 0.9300 . ?
C24 C23 1.517(4) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C19 C20 1.509(4) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 C21 1.533(5) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C12 C13 1.381(5) . ?
C12 H12 0.9300 . ?
C7 C6 1.398(5) . ?
C7 H7 0.9300 . ?
C6 H6 0.9300 . ?
C23 C22 1.529(5) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C13 H13 0.9300 . ?
C21 C22 1.513(4) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?

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 N1 C3 104.1(2) . . ?
C1 O1 C16 103.2(2) . . ?
C1 N2 C19 118.6(3) . . ?
C1 N2 C24 118.8(3) . . ?
C19 N2 C24 122.5(3) . . ?
N1 C1 N2 123.7(3) . . ?
N1 C1 O1 115.1(3) . . ?
N2 C1 O1 121.3(3) . . ?
C16 C3 N1 109.1(2) . . ?
C16 C3 C4 122.7(3) . . ?
N1 C3 C4 128.1(2) . . ?
C3 C16 O1 108.5(2) . . ?
C3 C16 C15 123.3(3) . . ?
O1 C16 C15 128.2(3) . . ?
C14 C15 C16 123.2(3) . . ?
C14 C15 C10 120.4(3) . . ?
C16 C15 C10 116.4(2) . . ?
C8 C9 C4 117.2(3) . . ?
C8 C9 C10 122.6(3) . . ?
C4 C9 C10 120.2(2) . . ?
C5 C4 C9 120.5(3) . . ?
C5 C4 C3 122.8(3) . . ?
C9 C4 C3 116.7(3) . . ?
C11 C10 C15 116.7(3) . . ?
C11 C10 C9 122.6(3) . . ?
C15 C10 C9 120.8(2) . . ?
C7 C8 C9 121.7(3) . . ?
C7 C8 H8 119.1 . . ?
C9 C8 H8 119.1 . . ?
C6 C5 C4 120.0(3) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C13 C14 C15 120.8(3) . . ?
C13 C14 H14 119.6 . . ?
C15 C14 H14 119.6 . . ?
C12 C11 C10 121.4(3) . . ?
C12 C11 H11 119.3 . . ?
C10 C11 H11 119.3 . . ?
N2 C24 C23 114.1(3) . . ?
N2 C24 H24A 108.7 . . ?
C23 C24 H24A 108.7 . . ?
N2 C24 H24B 108.7 . . ?
C23 C24 H24B 108.7 . . ?
H24A C24 H24B 107.6 . . ?
N2 C19 C20 113.6(3) . . ?
N2 C19 H19A 108.8 . . ?
C20 C19 H19A 108.8 . . ?
N2 C19 H19B 108.8 . . ?
C20 C19 H19B 108.8 . . ?
H19A C19 H19B 107.7 . . ?
C19 C20 C21 113.3(3) . . ?
C19 C20 H20A 108.9 . . ?
C21 C20 H20A 108.9 . . ?
C19 C20 H20B 108.9 . . ?
C21 C20 H20B 108.9 . . ?
H20A C20 H20B 107.7 . . ?
C11 C12 C13 120.9(3) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 H12 119.6 . . ?
C8 C7 C6 120.6(3) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C5 C6 C7 119.9(3) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
C24 C23 C22 114.7(3) . . ?
C24 C23 H23A 108.6 . . ?
C22 C23 H23A 108.6 . . ?
C24 C23 H23B 108.6 . . ?
C22 C23 H23B 108.6 . . ?
H23A C23 H23B 107.6 . . ?
C14 C13 C12 119.8(3) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C22 C21 C20 114.6(3) . . ?
C22 C21 H21A 108.6 . . ?
C20 C21 H21A 108.6 . . ?
C22 C21 H21B 108.6 . . ?
C20 C21 H21B 108.6 . . ?
H21A C21 H21B 107.6 . . ?
C21 C22 C23 114.0(3) . . ?
C21 C22 H22A 108.8 . . ?
C23 C22 H22A 108.8 . . ?
C21 C22 H22B 108.8 . . ?
C23 C22 H22B 108.8 . . ?
H22A C22 H22B 107.7 . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.206
_refine_diff_density_min         -0.141
_refine_diff_density_rms         0.037

####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2144928'
loop_
_audit_author_name
_audit_author_address
'Subhra Kanti Roy' 'Indian Institute of Technology, Guwahati'
_audit_update_record             
;
2022-01-27 deposited with the CCDC.	2022-04-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        2-(azepan-1-yl)naphtho[2,1-d]oxazole
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H18 N2 O'
_chemical_compound_source        synthesis
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethyl acetate and hexane'
_chemical_melting_point          ?

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_diffrn_ambient_temperature      296(2)
_chemical_formula_weight         266.33

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                   5.3217(4)
_cell_length_b                   26.6790(17)
_cell_length_c                   10.0784(6)
_cell_angle_alpha                90
_cell_angle_beta                 102.466(4)
_cell_angle_gamma                90
_cell_volume                     1397.17(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    16553
_cell_measurement_theta_min      1.53
_cell_measurement_theta_max      25.00
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.266
_exptl_crystal_F_000             568
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.32
_exptl_absorpt_coefficient_mu    0.080
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.970
_exptl_absorpt_correction_T_max  0.975
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15150
_diffrn_reflns_av_unetI/netI     0.0231
_diffrn_reflns_av_R_equivalents  0.0373
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         1.527
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2462
_reflns_number_gt                1824
_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.1006P)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     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.024(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2462
_refine_ls_number_parameters     182
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0837
_refine_ls_R_factor_gt           0.0658
_refine_ls_wR_factor_ref         0.2268
_refine_ls_wR_factor_gt          0.2117
_refine_ls_goodness_of_fit_ref   1.593
_refine_ls_restrained_S_all      1.593
_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 0.8628(3) 0.14216(6) 0.48938(16) 0.0593(5) Uani 1 1 d . . . . .
N1 N 0.7392(4) 0.06090(7) 0.46389(19) 0.0582(6) Uani 1 1 d . . . . .
N2 N 1.0319(4) 0.09366(8) 0.3402(2) 0.0654(7) Uani 1 1 d . . . . .
C1 C 0.6905(6) 0.21706(9) 0.6835(3) 0.0724(8) Uani 1 1 d . . . . .
H1 H 0.805629 0.230729 0.635921 0.087 Uiso 1 1 calc R U . . .
C2 C 0.5979(7) 0.24609(11) 0.7730(3) 0.0873(10) Uani 1 1 d . . . . .
H2 H 0.653783 0.279048 0.787982 0.105 Uiso 1 1 calc R U . . .
C3 C 0.4193(7) 0.22673(12) 0.8427(3) 0.0874(10) Uani 1 1 d . . . . .
H3 H 0.354957 0.246968 0.902777 0.105 Uiso 1 1 calc R U . . .
C4 C 0.3396(6) 0.17856(11) 0.8229(3) 0.0738(8) Uani 1 1 d . . . . .
H4 H 0.220073 0.166283 0.869829 0.089 Uiso 1 1 calc R U . . .
C5 C 0.4324(5) 0.14667(9) 0.7336(2) 0.0595(7) Uani 1 1 d . . . . .
C6 C 0.6147(5) 0.16652(9) 0.6616(2) 0.0569(7) Uani 1 1 d . . . . .
C7 C 0.3547(5) 0.09561(9) 0.7144(2) 0.0620(7) Uani 1 1 d . . . . .
H7 H 0.235365 0.083276 0.761318 0.074 Uiso 1 1 calc R U . . .
C8 C 0.4476(5) 0.06417(10) 0.6302(2) 0.0605(7) Uani 1 1 d . . . . .
H8 H 0.395572 0.030848 0.620397 0.073 Uiso 1 1 calc R U . . .
C9 C 0.6230(5) 0.08345(9) 0.5593(2) 0.0537(6) Uani 1 1 d . . . . .
C10 C 0.6979(5) 0.13267(9) 0.5762(2) 0.0538(6) Uani 1 1 d . . . . .
C11 C 0.8773(5) 0.09666(9) 0.4288(2) 0.0560(7) Uani 1 1 d . . . . .
C12 C 1.1567(6) 0.13649(12) 0.2954(3) 0.0789(9) Uani 1 1 d . . . . .
H12A H 1.338969 0.129300 0.307602 0.095 Uiso 1 1 calc R U . . .
H12B H 1.139074 0.164816 0.353079 0.095 Uiso 1 1 calc R U . . .
C13 C 1.0554(10) 0.15092(14) 0.1524(4) 0.1149(14) Uani 1 1 d . . . . .
H13A H 0.951689 0.180690 0.154471 0.138 Uiso 1 1 calc R U . . .
H13B H 1.202620 0.161290 0.116749 0.138 Uiso 1 1 calc R U . . .
C14 C 0.9115(11) 0.1193(3) 0.0560(5) 0.210(4) Uani 1 1 d . . . . .
H14A H 0.763236 0.139776 0.016935 0.252 Uiso 1 1 calc R U . . .
H14B H 1.012546 0.117891 -0.013318 0.252 Uiso 1 1 calc R U . . .
C15 C 0.8120(11) 0.07363(18) 0.0518(4) 0.146(2) Uani 1 1 d . . . . .
H15A H 0.853789 0.058137 -0.027832 0.175 Uiso 1 1 calc R U . . .
H15B H 0.627191 0.078699 0.029772 0.175 Uiso 1 1 calc R U . . .
C16 C 0.8550(7) 0.03403(15) 0.1561(3) 0.0958(10) Uani 1 1 d . . . . .
H16A H 0.899804 0.003322 0.115142 0.115 Uiso 1 1 calc R U . . .
H16B H 0.694615 0.028095 0.184475 0.115 Uiso 1 1 calc R U . . .
C17 C 1.0616(6) 0.04498(11) 0.2807(3) 0.0736(8) Uani 1 1 d . . . . .
H17A H 1.058202 0.019179 0.348118 0.088 Uiso 1 1 calc R U . . .
H17B H 1.228312 0.043572 0.256519 0.088 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 1.369(3) . ?
O1 C10 1.390(3) . ?
N1 C11 1.299(3) . ?
N1 C9 1.388(3) . ?
N2 C11 1.341(3) . ?
N2 C12 1.442(3) . ?
N2 C17 1.453(3) . ?
C1 C2 1.360(4) . ?
C1 C6 1.411(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.397(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.355(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.404(4) . ?
C4 H4 0.9300 . ?
C5 C7 1.425(3) . ?
C5 C6 1.432(4) . ?
C6 C10 1.384(3) . ?
C7 C8 1.360(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.391(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.372(3) . ?
C12 C13 1.477(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.386(7) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.326(7) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.473(5) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.508(4) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?

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 C10 102.89(17) . . ?
C11 N1 C9 103.5(2) . . ?
C11 N2 C12 123.5(2) . . ?
C11 N2 C17 117.7(2) . . ?
C12 N2 C17 118.7(2) . . ?
C2 C1 C6 121.0(3) . . ?
C2 C1 H1 119.5 . . ?
C6 C1 H1 119.5 . . ?
C1 C2 C3 120.4(3) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
C4 C3 C2 120.2(3) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C5 121.8(3) . . ?
C3 C4 H4 119.1 . . ?
C5 C4 H4 119.1 . . ?
C4 C5 C7 122.3(3) . . ?
C4 C5 C6 118.1(2) . . ?
C7 C5 C6 119.6(2) . . ?
C10 C6 C1 127.0(3) . . ?
C10 C6 C5 114.6(2) . . ?
C1 C6 C5 118.4(2) . . ?
C8 C7 C5 122.7(2) . . ?
C8 C7 H7 118.6 . . ?
C5 C7 H7 118.6 . . ?
C7 C8 C9 117.9(2) . . ?
C7 C8 H8 121.1 . . ?
C9 C8 H8 121.1 . . ?
C10 C9 N1 109.9(2) . . ?
C10 C9 C8 119.9(2) . . ?
N1 C9 C8 130.1(2) . . ?
C9 C10 C6 125.4(2) . . ?
C9 C10 O1 107.6(2) . . ?
C6 C10 O1 127.0(2) . . ?
N1 C11 N2 127.0(2) . . ?
N1 C11 O1 116.1(2) . . ?
N2 C11 O1 116.9(2) . . ?
N2 C12 C13 114.6(3) . . ?
N2 C12 H12A 108.6 . . ?
C13 C12 H12A 108.6 . . ?
N2 C12 H12B 108.6 . . ?
C13 C12 H12B 108.6 . . ?
H12A C12 H12B 107.6 . . ?
C14 C13 C12 123.8(3) . . ?
C14 C13 H13A 106.4 . . ?
C12 C13 H13A 106.4 . . ?
C14 C13 H13B 106.4 . . ?
C12 C13 H13B 106.4 . . ?
H13A C13 H13B 106.5 . . ?
C15 C14 C13 137.6(4) . . ?
C15 C14 H14A 102.7 . . ?
C13 C14 H14A 102.7 . . ?
C15 C14 H14B 102.7 . . ?
C13 C14 H14B 102.7 . . ?
H14A C14 H14B 105.0 . . ?
C14 C15 C16 129.6(4) . . ?
C14 C15 H15A 104.9 . . ?
C16 C15 H15A 104.9 . . ?
C14 C15 H15B 104.9 . . ?
C16 C15 H15B 104.9 . . ?
H15A C15 H15B 105.8 . . ?
C15 C16 C17 115.4(3) . . ?
C15 C16 H16A 108.4 . . ?
C17 C16 H16A 108.4 . . ?
C15 C16 H16B 108.4 . . ?
C17 C16 H16B 108.4 . . ?
H16A C16 H16B 107.5 . . ?
N2 C17 C16 113.1(2) . . ?
N2 C17 H17A 109.0 . . ?
C16 C17 H17A 109.0 . . ?
N2 C17 H17B 109.0 . . ?
C16 C17 H17B 109.0 . . ?
H17A C17 H17B 107.8 . . ?

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
C6 C1 C2 C3 -1.8(4) . . . . ?
C1 C2 C3 C4 0.9(5) . . . . ?
C2 C3 C4 C5 0.2(4) . . . . ?
C3 C4 C5 C7 178.5(3) . . . . ?
C3 C4 C5 C6 -0.5(4) . . . . ?
C2 C1 C6 C10 -178.5(2) . . . . ?
C2 C1 C6 C5 1.5(4) . . . . ?
C4 C5 C6 C10 179.64(19) . . . . ?
C7 C5 C6 C10 0.6(3) . . . . ?
C4 C5 C6 C1 -0.3(3) . . . . ?
C7 C5 C6 C1 -179.4(2) . . . . ?
C4 C5 C7 C8 -178.6(2) . . . . ?
C6 C5 C7 C8 0.4(4) . . . . ?
C5 C7 C8 C9 -0.9(4) . . . . ?
C11 N1 C9 C10 0.4(2) . . . . ?
C11 N1 C9 C8 178.0(2) . . . . ?
C7 C8 C9 C10 0.4(3) . . . . ?
C7 C8 C9 N1 -177.0(2) . . . . ?
N1 C9 C10 C6 178.6(2) . . . . ?
C8 C9 C10 C6 0.7(4) . . . . ?
N1 C9 C10 O1 0.6(3) . . . . ?
C8 C9 C10 O1 -177.31(19) . . . . ?
C1 C6 C10 C9 178.8(2) . . . . ?
C5 C6 C10 C9 -1.2(3) . . . . ?
C1 C6 C10 O1 -3.6(4) . . . . ?
C5 C6 C10 O1 176.44(19) . . . . ?
C11 O1 C10 C9 -1.3(2) . . . . ?
C11 O1 C10 C6 -179.2(2) . . . . ?
C9 N1 C11 N2 178.6(2) . . . . ?
C9 N1 C11 O1 -1.3(3) . . . . ?
C12 N2 C11 N1 172.9(2) . . . . ?
C17 N2 C11 N1 -3.4(4) . . . . ?
C12 N2 C11 O1 -7.3(3) . . . . ?
C17 N2 C11 O1 176.5(2) . . . . ?
C10 O1 C11 N1 1.7(2) . . . . ?
C10 O1 C11 N2 -178.24(19) . . . . ?
C11 N2 C12 C13 -109.9(3) . . . . ?
C17 N2 C12 C13 66.3(4) . . . . ?
N2 C12 C13 C14 -18.7(7) . . . . ?
C12 C13 C14 C15 3.7(14) . . . . ?
C13 C14 C15 C16 -10.3(16) . . . . ?
C14 C15 C16 C17 -6.7(9) . . . . ?
C11 N2 C17 C16 85.9(3) . . . . ?
C12 N2 C17 C16 -90.5(3) . . . . ?
C15 C16 C17 N2 50.6(4) . . . . ?

_refine_diff_density_max         0.308
_refine_diff_density_min         -0.354
_refine_diff_density_rms         0.041

_symmetry_cell_setting           ?
_symmetry_space_group_name_h-m   ?
_symmetry_int_tables_number      ?
_chemical_absolute_configuration ?

