# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_HM_788_1_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2025279'
loop_
_audit_author_name
_audit_author_address
'Ranjan Jana'
;CSIR Indian Institute of Chemical Biology
India
;
_audit_update_record             
;
2020-08-25 deposited with the CCDC.	2022-04-14 downloaded from the CCDC.
;
_audit_creation_date             2020-08-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_chemical_name_systematic        HM_788
_chemical_formula_moiety         'C21 H19 N3'
_chemical_formula_sum            'C21 H19 N3'
_chemical_formula_weight         313.41
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.01920 0.00962 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.03256 0.01839 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   15.2933(10)
_cell_length_b                   5.6759(9)
_cell_length_c                   18.003(3)
_cell_angle_alpha                90
_cell_angle_beta                 99.217(8)
_cell_angle_gamma                90
_cell_volume                     1542.5(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8481
_cell_measurement_temperature    100
_cell_measurement_theta_max      70.802
_cell_measurement_theta_min      2.928
_exptl_absorpt_coefficient_mu    0.627
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.5593
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1643 before and 0.0888 after correction. The Ratio of minimum to maximum transmission is 0.7422. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            'clear light white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.3495
_exptl_crystal_description       block
_exptl_crystal_F_000             665.8690
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_diffrn_reflns_av_R_equivalents  0.0804
_diffrn_reflns_av_unetI/netI     0.0465
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            22846
_diffrn_reflns_theta_full        71.8530
_diffrn_reflns_theta_max         71.85
_diffrn_reflns_theta_min         2.93
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.9741
_diffrn_measured_fraction_theta_max 0.9741
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              18
_reflns_limit_h_min              -18
_reflns_limit_k_max              6
_reflns_limit_k_min              0
_reflns_limit_l_max              22
_reflns_limit_l_min              0
_reflns_number_gt                2676
_reflns_number_total             2934
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.2232
_refine_diff_density_min         -0.3427
_refine_diff_density_rms         0.0628
_refine_ls_d_res_high            0.8112
_refine_ls_d_res_low             15.0958
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_goodness_of_fit_ref   1.0483
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    34
_refine_ls_number_parameters     218
_refine_ls_number_reflns         2934
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0570
_refine_ls_R_factor_gt           0.0531
_refine_ls_restrained_S_all      1.0483
_refine_ls_shift/su_max          0.0003
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0759P)²+0.7325P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1361
_refine_ls_wR_factor_ref         0.1400
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C00L(H00o)
2.b Secondary CH2 refined with riding coordinates:
 C00D(H00a,H00d), C00F(H00f,H00g), C00G(H00h,H00i), C00K(H00m,H00n)
2.c Aromatic/amide H refined with riding coordinates:
 C009(H009), C00B(H00B), C00C(H00C), C00E(H00E), C00H(H00j), C00I(H00k),
 C00J(H00l), C00M(H00p), C00N(H00q), C00O(H00r)
;
_atom_sites_solution_primary     iterative
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_refinement_flags_posn
N001 N 0.74235(9) 0.6676(2) 0.74910(7) 0.0225(3) Uani 1.000000 .
N002 N 0.72006(9) 0.5708(2) 0.62608(7) 0.0221(3) Uani 1.000000 .
N003 N 0.56326(9) 0.8895(2) 0.61197(8) 0.0242(3) Uani 1.000000 .
C004 C 0.79588(10) 0.4813(3) 0.73779(9) 0.0214(4) Uani 1.000000 .
C005 C 0.69745(10) 0.7154(3) 0.68125(9) 0.0214(4) Uani 1.000000 .
C006 C 0.78263(10) 0.4148(3) 0.66220(9) 0.0218(4) Uani 1.000000 .
C007 C 0.62948(11) 0.9016(3) 0.67118(9) 0.0221(4) Uani 1.000000 .
C008 C 0.85609(10) 0.3550(3) 0.79254(9) 0.0216(4) Uani 1.000000 .
C009 C 0.82410(11) 0.2144(3) 0.63653(9) 0.0235(4) Uani 1.000000 .
H009 H 0.81462(11) 0.1718(3) 0.58483(9) 0.0281(5) Uiso 1.000000 R
C00A C 0.89597(11) 0.1504(3) 0.76689(9) 0.0233(4) Uani 1.000000 .
C00B C 0.50258(11) 1.0621(3) 0.60562(9) 0.0254(4) Uani 1.000000 .
H00B H 0.45591(11) 1.0574(3) 0.56390(9) 0.0305(5) Uiso 1.000000 R
C00C C 0.50370(11) 1.2465(3) 0.65598(10) 0.0262(4) Uani 1.000000 .
H00C H 0.45902(11) 1.3643(3) 0.64896(10) 0.0314(5) Uiso 1.000000 R
C00D C 0.73696(11) 0.5570(3) 0.42228(9) 0.0245(4) Uani 1.000000 .
H00a H 0.78532(11) 0.5248(3) 0.39314(9) 0.0294(5) Uiso 1.000000 R
H00d H 0.69710(11) 0.6783(3) 0.39579(9) 0.0294(5) Uiso 1.000000 R
C00E C 0.57183(11) 1.2552(3) 0.71715(9) 0.0251(4) Uani 1.000000 .
H00E H 0.57446(11) 1.3789(3) 0.75299(9) 0.0301(5) Uiso 1.000000 R
C00F C 0.68598(12) 0.3315(3) 0.43437(9) 0.0269(4) Uani 1.000000 .
H00f H 0.63903(12) 0.3012(3) 0.39078(9) 0.0323(5) Uiso 1.000000 R
H00g H 0.72642(12) 0.1942(3) 0.44128(9) 0.0323(5) Uiso 1.000000 R
C00G C 0.77360(11) 0.6338(3) 0.50238(9) 0.0251(4) Uani 1.000000 .
H00h H 0.82518(11) 0.5366(3) 0.52403(9) 0.0302(5) Uiso 1.000000 R
H00i H 0.79126(11) 0.8018(3) 0.50410(9) 0.0302(5) Uiso 1.000000 R
C00H C 0.63560(11) 1.0808(3) 0.72488(9) 0.0235(4) Uani 1.000000 .
H00j H 0.68290(11) 1.0828(3) 0.76611(9) 0.0282(5) Uiso 1.000000 R
C00I C 0.87843(11) 0.0841(3) 0.68897(9) 0.0240(4) Uani 1.000000 .
H00k H 0.90530(11) -0.0542(3) 0.67329(9) 0.0288(5) Uiso 1.000000 R
C00J C 0.87695(11) 0.4236(3) 0.86837(9) 0.0242(4) Uani 1.000000 .
H00l H 0.85105(11) 0.5618(3) 0.88526(9) 0.0290(5) Uiso 1.000000 R
C00K C 0.64536(11) 0.3764(3) 0.50587(9) 0.0254(4) Uani 1.000000 .
H00m H 0.58114(11) 0.4090(3) 0.49289(9) 0.0304(5) Uiso 1.000000 R
H00n H 0.65386(11) 0.2378(3) 0.53967(9) 0.0304(5) Uiso 1.000000 R
C00L C 0.69475(11) 0.5929(3) 0.54400(9) 0.0233(4) Uani 1.000000 .
H00o H 0.65436(11) 0.7318(3) 0.53400(9) 0.0280(5) Uiso 1.000000 R
C00M C 0.95406(11) 0.0174(3) 0.82002(10) 0.0258(4) Uani 1.000000 .
H00p H 0.98031(11) -0.1219(3) 0.80431(10) 0.0310(5) Uiso 1.000000 R
C00N C 0.93489(11) 0.2912(3) 0.91837(10) 0.0272(4) Uani 1.000000 .
H00q H 0.94900(11) 0.3387(3) 0.96950(10) 0.0326(5) Uiso 1.000000 R
C00O C 0.97300(11) 0.0864(3) 0.89371(10) 0.0279(4) Uani 1.000000 .
H00r H 1.01229(11) -0.0052(3) 0.92848(10) 0.0335(5) Uiso 1.000000 R


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
N001 C004 1.372(2) . ?
N001 C005 1.330(2) . ?
N002 C005 1.375(2) . ?
N002 C006 1.387(2) . ?
N002 C00L 1.472(2) . ?
N003 C007 1.349(2) . ?
N003 C00B 1.342(2) . ?
C004 C006 1.395(2) . ?
C004 C008 1.429(2) . ?
C005 C007 1.473(2) . ?
C006 C009 1.415(2) . ?
C007 C00H 1.396(2) . ?
C008 C00A 1.423(2) . ?
C008 C00J 1.406(2) . ?
C009 H009 0.9500 . ?
C009 C00I 1.370(2) . ?
C00A C00I 1.436(2) . ?
C00A C00M 1.415(2) . ?
C00B H00B 0.9500 . ?
C00B C00C 1.383(2) . ?
C00C H00C 0.9500 . ?
C00C C00E 1.390(2) . ?
C00D H00a 0.9900 . ?
C00D H00d 0.9900 . ?
C00D C00F 1.532(2) . ?
C00D C00G 1.525(2) . ?
C00E H00E 0.9500 . ?
C00E C00H 1.381(2) . ?
C00F H00f 0.9900 . ?
C00F H00g 0.9900 . ?
C00F C00K 1.538(2) . ?
C00G H00h 0.9900 . ?
C00G H00i 0.9900 . ?
C00G C00L 1.536(2) . ?
C00H H00j 0.9500 . ?
C00I H00k 0.9500 . ?
C00J H00l 0.9500 . ?
C00J C00N 1.380(2) . ?
C00K H00m 0.9900 . ?
C00K H00n 0.9900 . ?
C00K C00L 1.544(2) . ?
C00L H00o 1.0000 . ?
C00M H00p 0.9500 . ?
C00M C00O 1.369(2) . ?
C00N H00q 0.9500 . ?
C00N C00O 1.404(3) . ?
C00O H00r 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
C005 N001 C004 104.69(13) . . ?
C006 N002 C005 106.08(13) . . ?
C00L N002 C005 128.21(13) . . ?
C00L N002 C006 125.16(13) . . ?
C00B N003 C007 116.82(14) . . ?
C006 C004 N001 110.87(14) . . ?
C008 C004 N001 128.16(14) . . ?
C008 C004 C006 120.93(15) . . ?
N002 C005 N001 112.90(14) . . ?
C007 C005 N001 120.65(14) . . ?
C007 C005 N002 126.42(14) . . ?
C004 C006 N002 105.43(14) . . ?
C009 C006 N002 132.20(15) . . ?
C009 C006 C004 122.21(15) . . ?
C005 C007 N003 119.07(14) . . ?
C00H C007 N003 122.88(15) . . ?
C00H C007 C005 118.03(14) . . ?
C00A C008 C004 116.61(14) . . ?
C00J C008 C004 123.47(15) . . ?
C00J C008 C00A 119.92(15) . . ?
H009 C009 C006 121.22(9) . . ?
C00I C009 C006 117.57(15) . . ?
C00I C009 H009 121.22(10) . . ?
C00I C00A C008 120.55(15) . . ?
C00M C00A C008 118.13(15) . . ?
C00M C00A C00I 121.30(15) . . ?
H00B C00B N003 117.94(9) . . ?
C00C C00B N003 124.12(15) . . ?
C00C C00B H00B 117.94(10) . . ?
H00C C00C C00B 120.82(10) . . ?
C00E C00C C00B 118.37(15) . . ?
C00E C00C H00C 120.82(10) . . ?
H00d C00D H00a 109.1 . . ?
C00F C00D H00a 111.19(9) . . ?
C00F C00D H00d 111.19(9) . . ?
C00G C00D H00a 111.19(9) . . ?
C00G C00D H00d 111.19(9) . . ?
C00G C00D C00F 102.88(13) . . ?
H00E C00E C00C 120.59(10) . . ?
C00H C00E C00C 118.82(15) . . ?
C00H C00E H00E 120.59(10) . . ?
H00f C00F C00D 110.69(9) . . ?
H00g C00F C00D 110.69(9) . . ?
H00g C00F H00f 108.8 . . ?
C00K C00F C00D 105.27(13) . . ?
C00K C00F H00f 110.69(9) . . ?
C00K C00F H00g 110.69(9) . . ?
H00h C00G C00D 111.23(9) . . ?
H00i C00G C00D 111.23(9) . . ?
H00i C00G H00h 109.1 . . ?
C00L C00G C00D 102.69(13) . . ?
C00L C00G H00h 111.23(9) . . ?
C00L C00G H00i 111.23(9) . . ?
C00E C00H C007 118.98(15) . . ?
H00j C00H C007 120.51(10) . . ?
H00j C00H C00E 120.51(10) . . ?
C00A C00I C009 121.98(15) . . ?
H00k C00I C009 119.01(10) . . ?
H00k C00I C00A 119.01(9) . . ?
H00l C00J C008 119.85(9) . . ?
C00N C00J C008 120.29(16) . . ?
C00N C00J H00l 119.85(10) . . ?
H00m C00K C00F 110.61(9) . . ?
H00n C00K C00F 110.61(9) . . ?
H00n C00K H00m 108.7 . . ?
C00L C00K C00F 105.64(13) . . ?
C00L C00K H00m 110.61(9) . . ?
C00L C00K H00n 110.61(8) . . ?
C00G C00L N002 113.69(13) . . ?
C00K C00L N002 114.20(13) . . ?
C00K C00L C00G 105.65(13) . . ?
H00o C00L N002 107.66(8) . . ?
H00o C00L C00G 107.66(9) . . ?
H00o C00L C00K 107.66(9) . . ?
H00p C00M C00A 119.50(10) . . ?
C00O C00M C00A 121.00(16) . . ?
C00O C00M H00p 119.50(10) . . ?
H00q C00N C00J 119.99(10) . . ?
C00O C00N C00J 120.02(16) . . ?
C00O C00N H00q 119.99(10) . . ?
C00N C00O C00M 120.60(16) . . ?
H00r C00O C00M 119.70(10) . . ?
H00r C00O C00N 119.70(10) . . ?


_olex2_submission_special_instructions 'No special instructions were received'
_chemical_name_common            
3-cyclopentyl-2-(pyridin-2-yl)-3H-naphtho[1,2-d]imidazole
_chemical_melting_point          418
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane, petroleum ether'
####################################################################### 
# 
# 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_hm_643s_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2025280'
loop_
_audit_author_name
_audit_author_address
'Ranjan Jana'
;CSIR Indian Institute of Chemical Biology
India
;
_audit_update_record             
;
2020-08-25 deposited with the CCDC.	2022-04-14 downloaded from the CCDC.
;
_audit_creation_date             2020-07-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            HM
_chemical_name_systematic        HM-643S
_chemical_formula_moiety         'C16 H12 N2 S'
_chemical_formula_sum            'C16 H12 N2 S'
_chemical_formula_weight         264.34
_chemical_melting_point          398
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   6.1282(2)
_cell_length_b                   14.1422(4)
_cell_length_c                   14.4603(4)
_cell_angle_alpha                90
_cell_angle_beta                 95.2550(10)
_cell_angle_gamma                90
_cell_volume                     1247.95(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9927
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      66.819
_cell_measurement_theta_min      4.382
_shelx_estimated_absorpt_T_max   0.671
_shelx_estimated_absorpt_T_min   0.671
_exptl_absorpt_coefficient_mu    2.167
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.6618
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1175 before and 0.0649 after correction. The Ratio of minimum to maximum transmission is 0.8791. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   Nothing
_exptl_crystal_colour            'clear light white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       chloroform
_exptl_crystal_F_000             552
_exptl_crystal_preparation       'in CHCl3'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: chloroform'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0469
_diffrn_reflns_av_unetI/netI     0.0251
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            19122
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        66.813
_diffrn_reflns_theta_max         66.813
_diffrn_reflns_theta_min         4.382
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_special_details          No
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2132
_reflns_number_total             2213
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2213
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0373
_refine_ls_R_factor_gt           0.0361
_refine_ls_restrained_S_all      1.078
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0416P)²+0.8469P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0921
_refine_ls_wR_factor_ref         0.0929
_refine_special_details          No
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N002(H002), C008(H008), C00A(H00A), C00B(H00B), C00C(H00C), C00D(H00D),
 C00E(H00E), C00F(H00F), C00G(H00G), C00H(H00H), C00I(H00I), C00J(H00J)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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
S001 S 0.32381(7) 0.73439(3) 0.51266(3) 0.02613(16) Uani 1 1 d . . . . .
N002 N 0.2431(2) 0.67280(9) 0.68340(9) 0.0175(3) Uani 1 1 d . . . . .
H002 H 0.297589 0.673681 0.741861 0.021 Uiso 1 1 calc R . . . .
N003 N 0.5461(2) 0.76710(9) 0.77541(9) 0.0189(3) Uani 1 1 d . . . . .
C004 C 0.5528(3) 0.76989(11) 0.68265(11) 0.0177(3) Uani 1 1 d . . . . .
C005 C 0.0489(2) 0.62000(11) 0.66875(11) 0.0173(3) Uani 1 1 d . . . . .
C006 C -0.2565(3) 0.54361(11) 0.73852(11) 0.0195(3) Uani 1 1 d . . . . .
C007 C -0.0531(2) 0.59302(11) 0.75054(11) 0.0175(3) Uani 1 1 d . . . . .
C008 C -0.2426(3) 0.54441(12) 0.57237(12) 0.0235(4) Uani 1 1 d . . . . .
H008 H -0.304769 0.527077 0.512158 0.028 Uiso 1 1 calc R . . . .
C009 C 0.3634(3) 0.72223(11) 0.62712(11) 0.0178(3) Uani 1 1 d . . . . .
C00A C -0.0713(3) 0.58789(12) 0.91763(11) 0.0232(4) Uani 1 1 d . . . . .
H00A H -0.008155 0.602099 0.978500 0.028 Uiso 1 1 calc R . . . .
C00B C 0.0356(3) 0.61339(11) 0.84234(11) 0.0192(3) Uani 1 1 d . . . . .
H00B H 0.172125 0.645399 0.851838 0.023 Uiso 1 1 calc R . . . .
C00C C 0.7223(3) 0.81233(11) 0.64053(11) 0.0204(4) Uani 1 1 d . . . . .
H00C H 0.722396 0.812882 0.574836 0.024 Uiso 1 1 calc R . . . .
C00D C 0.7109(3) 0.80709(12) 0.82845(11) 0.0212(4) Uani 1 1 d . . . . .
H00D H 0.707890 0.805109 0.893992 0.025 Uiso 1 1 calc R . . . .
C00E C -0.3481(3) 0.51976(12) 0.64809(12) 0.0223(4) Uani 1 1 d . . . . .
H00E H -0.483197 0.486515 0.640022 0.027 Uiso 1 1 calc R . . . .
C00F C -0.0449(3) 0.59469(12) 0.58160(11) 0.0213(4) Uani 1 1 d . . . . .
H00F H 0.025001 0.611432 0.527931 0.026 Uiso 1 1 calc R . . . .
C00G C 0.8865(3) 0.85145(12) 0.79209(12) 0.0231(4) Uani 1 1 d . . . . .
H00G H 1.000605 0.879434 0.831873 0.028 Uiso 1 1 calc R . . . .
C00H C -0.2747(3) 0.54061(13) 0.90530(12) 0.0259(4) Uani 1 1 d . . . . .
H00H H -0.349349 0.523932 0.957702 0.031 Uiso 1 1 calc R . . . .
C00I C -0.3637(3) 0.51894(12) 0.81809(12) 0.0233(4) Uani 1 1 d . . . . .
H00I H -0.500179 0.486699 0.810366 0.028 Uiso 1 1 calc R . . . .
C00J C 0.8915(3) 0.85395(12) 0.69657(12) 0.0230(4) Uani 1 1 d . . . . .
H00J H 1.009464 0.883802 0.669731 0.028 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
S001 C009 1.6595(16) . ?
N002 H002 0.8800 . ?
N002 C005 1.405(2) . ?
N002 C009 1.343(2) . ?
N003 C004 1.346(2) . ?
N003 C00D 1.336(2) . ?
C004 C009 1.509(2) . ?
C004 C00C 1.388(2) . ?
C005 C007 1.439(2) . ?
C005 C00F 1.383(2) . ?
C006 C007 1.426(2) . ?
C006 C00E 1.416(2) . ?
C006 C00I 1.420(2) . ?
C007 C00B 1.417(2) . ?
C008 H008 0.9500 . ?
C008 C00E 1.367(2) . ?
C008 C00F 1.401(2) . ?
C00A H00A 0.9500 . ?
C00A C00B 1.369(2) . ?
C00A C00H 1.411(2) . ?
C00B H00B 0.9500 . ?
C00C H00C 0.9500 . ?
C00C C00J 1.387(2) . ?
C00D H00D 0.9500 . ?
C00D C00G 1.390(2) . ?
C00E H00E 0.9500 . ?
C00F H00F 0.9500 . ?
C00G H00G 0.9500 . ?
C00G C00J 1.385(2) . ?
C00H H00H 0.9500 . ?
C00H C00I 1.362(3) . ?
C00I H00I 0.9500 . ?
C00J H00J 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
C005 N002 H002 113.2 . . ?
C009 N002 H002 113.2 . . ?
C009 N002 C005 133.60(14) . . ?
C00D N003 C004 117.99(14) . . ?
N003 C004 C009 115.17(14) . . ?
N003 C004 C00C 122.82(15) . . ?
C00C C004 C009 122.01(14) . . ?
N002 C005 C007 116.29(14) . . ?
C00F C005 N002 123.39(14) . . ?
C00F C005 C007 120.32(15) . . ?
C00E C006 C007 119.84(15) . . ?
C00E C006 C00I 121.09(15) . . ?
C00I C006 C007 119.07(15) . . ?
C006 C007 C005 118.07(14) . . ?
C00B C007 C005 123.89(15) . . ?
C00B C007 C006 118.04(14) . . ?
C00E C008 H008 119.3 . . ?
C00E C008 C00F 121.44(16) . . ?
C00F C008 H008 119.3 . . ?
N002 C009 S001 128.33(13) . . ?
N002 C009 C004 110.37(13) . . ?
C004 C009 S001 121.30(12) . . ?
C00B C00A H00A 119.8 . . ?
C00B C00A C00H 120.38(16) . . ?
C00H C00A H00A 119.8 . . ?
C007 C00B H00B 119.3 . . ?
C00A C00B C007 121.37(15) . . ?
C00A C00B H00B 119.3 . . ?
C004 C00C H00C 120.8 . . ?
C00J C00C C004 118.47(15) . . ?
C00J C00C H00C 120.8 . . ?
N003 C00D H00D 118.5 . . ?
N003 C00D C00G 122.98(15) . . ?
C00G C00D H00D 118.5 . . ?
C006 C00E H00E 119.9 . . ?
C008 C00E C006 120.18(15) . . ?
C008 C00E H00E 119.9 . . ?
C005 C00F C008 120.10(15) . . ?
C005 C00F H00F 119.9 . . ?
C008 C00F H00F 119.9 . . ?
C00D C00G H00G 120.7 . . ?
C00J C00G C00D 118.52(15) . . ?
C00J C00G H00G 120.7 . . ?
C00A C00H H00H 120.1 . . ?
C00I C00H C00A 119.84(15) . . ?
C00I C00H H00H 120.1 . . ?
C006 C00I H00I 119.4 . . ?
C00H C00I C006 121.28(16) . . ?
C00H C00I H00I 119.4 . . ?
C00C C00J H00J 120.4 . . ?
C00G C00J C00C 119.22(15) . . ?
C00G C00J H00J 120.4 . . ?

_olex2_submission_original_sample_id HM-643S
_olex2_submission_special_instructions 'No special instructions were received'
_chemical_compound_source        synthetic
####################################################################### 
# 
# 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_hm_583_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2025269'
loop_
_audit_author_name
_audit_author_address
'Ranjan Jana'
;CSIR Indian Institute of Chemical Biology
India
;
_audit_update_record             
;
2020-08-25 deposited with the CCDC.	2022-04-14 downloaded from the CCDC.
;
_audit_creation_date             2020-07-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            
3-cyclohexyl-1-(5-methylpyrazin-2-yl)-1,3-dihydro-2H-naphtho[1,2-d]imidazol-2-one
_chemical_name_systematic        ?
_chemical_formula_moiety         '0.11(C22 H22 N4 O)'
_chemical_formula_sum            'C2.44 H2.44 N0.44 O0.11'
_chemical_formula_weight         39.83
_chemical_melting_point          408
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.9957(2)
_cell_length_b                   10.4307(2)
_cell_length_c                   12.5078(3)
_cell_angle_alpha                67.7270(10)
_cell_angle_beta                 89.0730(10)
_cell_angle_gamma                71.4000(10)
_cell_volume                     908.36(4)
_cell_formula_units_Z            18
_cell_measurement_reflns_used    9957
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      66.599
_cell_measurement_theta_min      3.846
_shelx_estimated_absorpt_T_max   0.842
_shelx_estimated_absorpt_T_min   0.621
_exptl_absorpt_coefficient_mu    0.658
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.6023
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1243 before and 0.0796 after correction. The Ratio of minimum to maximum transmission is 0.8001. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             380
_exptl_crystal_size_max          0.80
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.27
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0634
_diffrn_reflns_av_unetI/netI     0.0334
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            28821
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        66.701
_diffrn_reflns_theta_max         66.701
_diffrn_reflns_theta_min         3.846
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3086
_reflns_number_total             3182
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_refine_diff_density_max         0.206
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3182
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0438
_refine_ls_R_factor_gt           0.0424
_refine_ls_restrained_S_all      1.088
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0399P)²+0.3924P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0985
_refine_ls_wR_factor_ref         0.0994
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C00B(H00B)
2.b Secondary CH2 refined with riding coordinates:
 C00E(H00A,H00E), C00J(H00I,H00J), C00N(H00L,H00N), C00P(H00P,H00Q), C00Q(H00R,
 H00S)
2.c Aromatic/amide H refined with riding coordinates:
 C00C(H00C), C00D(H00D), C00F(H00F), C00G(H00G), C00H(H00H), C00K(H00K),
 C00M(H00M), C00O(H00O)
2.d Idealised Me refined as rotating group:
 C00R(H00T,H00U,H00V)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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
O001 O 0.31326(12) 0.35047(10) 0.84815(8) 0.0196(2) Uani 1 1 d . . . . .
N002 N 0.52338(14) 0.35658(12) 0.71503(10) 0.0158(3) Uani 1 1 d . . . . .
N003 N 0.78246(15) 0.38344(12) 0.77453(10) 0.0174(3) Uani 1 1 d . . . . .
N004 N 0.39374(15) 0.18638(12) 0.75630(10) 0.0167(3) Uani 1 1 d . . . . .
N005 N 0.57909(16) 0.63783(13) 0.80492(11) 0.0236(3) Uani 1 1 d . . . . .
C006 C 0.59390(17) 0.27184(15) 0.64993(12) 0.0162(3) Uani 1 1 d . . . . .
C007 C 0.39859(17) 0.30295(14) 0.78125(12) 0.0156(3) Uani 1 1 d . . . . .
C008 C 0.51433(17) 0.16540(15) 0.67708(12) 0.0165(3) Uani 1 1 d . . . . .
C009 C 0.60671(18) 0.43815(14) 0.75094(12) 0.0160(3) Uani 1 1 d . . . . .
C00A C 0.71046(17) 0.28964(15) 0.56325(12) 0.0164(3) Uani 1 1 d . . . . .
C00B C 0.29182(18) 0.09228(15) 0.82010(12) 0.0169(3) Uani 1 1 d . . . . .
H00B H 0.232652 0.132362 0.877291 0.020 Uiso 1 1 calc R . . . .
C00C C 0.85609(18) 0.45825(15) 0.81432(12) 0.0176(3) Uani 1 1 d . . . . .
H00C H 0.981726 0.424329 0.831265 0.021 Uiso 1 1 calc R . . . .
C00D C 0.55630(18) 0.06078(15) 0.62674(12) 0.0191(3) Uani 1 1 d . . . . .
H00D H 0.501182 -0.012131 0.645764 0.023 Uiso 1 1 calc R . . . .
C00E C 0.41353(18) -0.06542(15) 0.89002(12) 0.0182(3) Uani 1 1 d . . . . .
H00A H 0.473568 -0.109725 0.836242 0.022 Uiso 1 1 calc R . . . .
H00E H 0.506025 -0.064744 0.941273 0.022 Uiso 1 1 calc R . . . .
C00F C 0.88084(19) 0.18726(16) 0.43266(12) 0.0212(3) Uani 1 1 d . . . . .
H00F H 0.916546 0.113073 0.402315 0.025 Uiso 1 1 calc R . . . .
C00G C 0.67951(18) 0.06794(16) 0.54931(12) 0.0198(3) Uani 1 1 d . . . . .
H00G H 0.713950 -0.004501 0.517164 0.024 Uiso 1 1 calc R . . . .
C00H C 0.77850(18) 0.40769(15) 0.51948(12) 0.0188(3) Uani 1 1 d . . . . .
H00H H 0.743324 0.484178 0.547399 0.023 Uiso 1 1 calc R . . . .
C00I C 0.75635(18) 0.58328(15) 0.83182(12) 0.0191(3) Uani 1 1 d . . . . .
C00J C 0.14484(18) 0.09606(15) 0.74125(12) 0.0198(3) Uani 1 1 d . . . . .
H00I H 0.066279 0.199025 0.698236 0.024 Uiso 1 1 calc R . . . .
H00J H 0.197856 0.055533 0.683831 0.024 Uiso 1 1 calc R . . . .
C00K C 0.89431(19) 0.41213(16) 0.43743(12) 0.0218(3) Uani 1 1 d . . . . .
H00K H 0.937988 0.492146 0.408366 0.026 Uiso 1 1 calc R . . . .
C00L C 0.75741(18) 0.17984(15) 0.51551(12) 0.0181(3) Uani 1 1 d . . . . .
C00M C 0.50512(19) 0.56482(15) 0.76450(13) 0.0217(3) Uani 1 1 d . . . . .
H00M H 0.379949 0.600472 0.744552 0.026 Uiso 1 1 calc R . . . .
C00N C 0.1542(2) -0.15231(16) 0.88878(13) 0.0236(3) Uani 1 1 d . . . . .
H00L H 0.081053 -0.205006 0.939906 0.028 Uiso 1 1 calc R . . . .
H00N H 0.203234 -0.203799 0.837122 0.028 Uiso 1 1 calc R . . . .
C00O C 0.94934(19) 0.29897(17) 0.39566(13) 0.0239(3) Uani 1 1 d . . . . .
H00O H 1.034310 0.300515 0.341629 0.029 Uiso 1 1 calc R . . . .
C00P C 0.03673(19) 0.00508(16) 0.81485(13) 0.0233(3) Uani 1 1 d . . . . .
H00P H -0.025927 0.052213 0.866348 0.028 Uiso 1 1 calc R . . . .
H00Q H -0.053992 0.003178 0.763069 0.028 Uiso 1 1 calc R . . . .
C00Q C 0.30706(19) -0.15747(16) 0.96348(12) 0.0216(3) Uani 1 1 d . . . . .
H00R H 0.258961 -0.119991 1.023441 0.026 Uiso 1 1 calc R . . . .
H00S H 0.386380 -0.260773 1.003791 0.026 Uiso 1 1 calc R . . . .
C00R C 0.8408(2) 0.66257(17) 0.88002(13) 0.0239(3) Uani 1 1 d . . . . .
H00T H 0.811222 0.764964 0.824561 0.036 Uiso 1 1 calc GR . . . .
H00U H 0.970065 0.614140 0.893076 0.036 Uiso 1 1 calc GR . . . .
H00V H 0.796170 0.660411 0.953903 0.036 Uiso 1 1 calc GR . . . .


_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
O001 C007 1.2212(16) . ?
N002 C006 1.4054(17) . ?
N002 C007 1.4044(17) . ?
N002 C009 1.4250(17) . ?
N003 C009 1.3273(18) . ?
N003 C00C 1.3418(18) . ?
N004 C007 1.3768(17) . ?
N004 C008 1.3993(17) . ?
N004 C00B 1.4695(17) . ?
N005 C00I 1.3423(18) . ?
N005 C00M 1.3319(19) . ?
C006 C008 1.3822(19) . ?
C006 C00A 1.4155(19) . ?
C008 C00D 1.4073(19) . ?
C009 C00M 1.3839(19) . ?
C00A C00H 1.4208(19) . ?
C00A C00L 1.430(2) . ?
C00B H00B 1.0000 . ?
C00B C00E 1.5276(19) . ?
C00B C00J 1.5277(19) . ?
C00C H00C 0.9500 . ?
C00C C00I 1.390(2) . ?
C00D H00D 0.9500 . ?
C00D C00G 1.369(2) . ?
C00E H00A 0.9900 . ?
C00E H00E 0.9900 . ?
C00E C00Q 1.5225(19) . ?
C00F H00F 0.9500 . ?
C00F C00L 1.4173(19) . ?
C00F C00O 1.365(2) . ?
C00G H00G 0.9500 . ?
C00G C00L 1.418(2) . ?
C00H H00H 0.9500 . ?
C00H C00K 1.369(2) . ?
C00I C00R 1.5001(19) . ?
C00J H00I 0.9900 . ?
C00J H00J 0.9900 . ?
C00J C00P 1.5266(19) . ?
C00K H00K 0.9500 . ?
C00K C00O 1.410(2) . ?
C00M H00M 0.9500 . ?
C00N H00L 0.9900 . ?
C00N H00N 0.9900 . ?
C00N C00P 1.525(2) . ?
C00N C00Q 1.525(2) . ?
C00O H00O 0.9500 . ?
C00P H00P 0.9900 . ?
C00P H00Q 0.9900 . ?
C00Q H00R 0.9900 . ?
C00Q H00S 0.9900 . ?
C00R H00T 0.9800 . ?
C00R H00U 0.9800 . ?
C00R H00V 0.9800 . ?

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
C006 N002 C009 126.62(11) . . ?
C007 N002 C006 109.10(11) . . ?
C007 N002 C009 119.48(11) . . ?
C009 N003 C00C 115.44(12) . . ?
C007 N004 C008 109.55(11) . . ?
C007 N004 C00B 121.47(11) . . ?
C008 N004 C00B 128.45(11) . . ?
C00M N005 C00I 117.12(12) . . ?
N002 C006 C00A 130.75(12) . . ?
C008 C006 N002 106.94(12) . . ?
C008 C006 C00A 122.06(12) . . ?
O001 C007 N002 126.33(12) . . ?
O001 C007 N004 127.35(13) . . ?
N004 C007 N002 106.32(11) . . ?
N004 C008 C00D 130.31(12) . . ?
C006 C008 N004 108.07(12) . . ?
C006 C008 C00D 121.61(13) . . ?
N003 C009 N002 116.86(12) . . ?
N003 C009 C00M 122.78(13) . . ?
C00M C009 N002 120.30(12) . . ?
C006 C00A C00H 125.40(13) . . ?
C006 C00A C00L 115.75(12) . . ?
C00H C00A C00L 118.83(13) . . ?
N004 C00B H00B 107.0 . . ?
N004 C00B C00E 111.44(11) . . ?
N004 C00B C00J 112.70(11) . . ?
C00E C00B H00B 107.0 . . ?
C00J C00B H00B 107.0 . . ?
C00J C00B C00E 111.26(11) . . ?
N003 C00C H00C 118.6 . . ?
N003 C00C C00I 122.79(12) . . ?
C00I C00C H00C 118.6 . . ?
C008 C00D H00D 121.2 . . ?
C00G C00D C008 117.55(13) . . ?
C00G C00D H00D 121.2 . . ?
C00B C00E H00A 109.6 . . ?
C00B C00E H00E 109.6 . . ?
H00A C00E H00E 108.1 . . ?
C00Q C00E C00B 110.50(11) . . ?
C00Q C00E H00A 109.6 . . ?
C00Q C00E H00E 109.6 . . ?
C00L C00F H00F 119.4 . . ?
C00O C00F H00F 119.4 . . ?
C00O C00F C00L 121.23(14) . . ?
C00D C00G H00G 118.9 . . ?
C00D C00G C00L 122.21(13) . . ?
C00L C00G H00G 118.9 . . ?
C00A C00H H00H 119.7 . . ?
C00K C00H C00A 120.56(13) . . ?
C00K C00H H00H 119.7 . . ?
N005 C00I C00C 120.42(13) . . ?
N005 C00I C00R 117.61(12) . . ?
C00C C00I C00R 121.97(13) . . ?
C00B C00J H00I 109.8 . . ?
C00B C00J H00J 109.8 . . ?
H00I C00J H00J 108.2 . . ?
C00P C00J C00B 109.55(11) . . ?
C00P C00J H00I 109.8 . . ?
C00P C00J H00J 109.8 . . ?
C00H C00K H00K 119.7 . . ?
C00H C00K C00O 120.57(13) . . ?
C00O C00K H00K 119.7 . . ?
C00F C00L C00A 118.46(13) . . ?
C00F C00L C00G 121.09(13) . . ?
C00G C00L C00A 120.44(13) . . ?
N005 C00M C009 121.41(13) . . ?
N005 C00M H00M 119.3 . . ?
C009 C00M H00M 119.3 . . ?
H00L C00N H00N 107.9 . . ?
C00P C00N H00L 109.2 . . ?
C00P C00N H00N 109.2 . . ?
C00Q C00N H00L 109.2 . . ?
C00Q C00N H00N 109.2 . . ?
C00Q C00N C00P 112.14(12) . . ?
C00F C00O C00K 120.17(13) . . ?
C00F C00O H00O 119.9 . . ?
C00K C00O H00O 119.9 . . ?
C00J C00P H00P 109.3 . . ?
C00J C00P H00Q 109.3 . . ?
C00N C00P C00J 111.70(12) . . ?
C00N C00P H00P 109.3 . . ?
C00N C00P H00Q 109.3 . . ?
H00P C00P H00Q 107.9 . . ?
C00E C00Q C00N 111.29(12) . . ?
C00E C00Q H00R 109.4 . . ?
C00E C00Q H00S 109.4 . . ?
C00N C00Q H00R 109.4 . . ?
C00N C00Q H00S 109.4 . . ?
H00R C00Q H00S 108.0 . . ?
C00I C00R H00T 109.5 . . ?
C00I C00R H00U 109.5 . . ?
C00I C00R H00V 109.5 . . ?
H00T C00R H00U 109.5 . . ?
H00T C00R H00V 109.5 . . ?
H00U C00R H00V 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane, petroleum ether'
####################################################################### 
# 
# 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_hm_430a_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2025266'
loop_
_audit_author_name
_audit_author_address
'Ranjan Jana'
;CSIR Indian Institute of Chemical Biology
India
;
_audit_update_record             
;
2020-08-25 deposited with the CCDC.	2022-04-14 downloaded from the CCDC.
;
_audit_creation_date             2020-08-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            
3-methyl-2-(pyridin-2-yl)-3H-naphtho[1,2-d]imidazole
_chemical_name_systematic        HM-430A
_chemical_formula_moiety         'C17 H13 N3'
_chemical_formula_sum            'C17 H13 N3'
_chemical_formula_weight         259.30
_chemical_melting_point          109
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   10.9333(3)
_cell_length_b                   7.3400(2)
_cell_length_c                   16.2518(5)
_cell_angle_alpha                90
_cell_angle_beta                 98.6550(10)
_cell_angle_gamma                90
_cell_volume                     1289.36(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2
_cell_measurement_temperature    100
_cell_measurement_theta_max      66.300
_cell_measurement_theta_min      2.750
_shelx_estimated_absorpt_T_max   0.883
_shelx_estimated_absorpt_T_min   0.883
_exptl_absorpt_coefficient_mu    0.638
_exptl_absorpt_correction_T_max  0.837
_exptl_absorpt_correction_T_min  .802
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1876 before and 0.0906 after correction. The Ratio of minimum to maximum transmission is 0.6493. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear whiteish white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             544
_exptl_crystal_preparation       Luminescent
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0807
_diffrn_reflns_av_unetI/netI     0.0459
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            18364
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        66.459
_diffrn_reflns_theta_max         66.459
_diffrn_reflns_theta_min         6.631
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2105
_reflns_number_total             2259
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.362
_refine_diff_density_min         -0.337
_refine_diff_density_rms         0.092
_refine_ls_extinction_coef       0.028(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2259
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0623
_refine_ls_R_factor_gt           0.0595
_refine_ls_restrained_S_all      1.072
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0959P)²+0.5135P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1563
_refine_ls_wR_factor_ref         0.1597
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C009(H009), C00B(H00B), C00C(H00C), C00D(H00D), C00E(H00E), C00G(H00H),
 C00H(H00I), C00I(H00J), C00J(H00K), C00K(H00L)
2.b Idealised Me refined as rotating group:
 C00F(H00A,H00F,H00G)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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
N2 N 0.52478(13) 0.2928(2) 0.36706(9) 0.0276(4) Uani 1 1 d . . . . .
N1 N 0.61942(13) 0.3176(2) 0.49956(9) 0.0266(4) Uani 1 1 d . . . . .
N003 N 0.84864(14) 0.3884(2) 0.42952(10) 0.0373(5) Uani 1 1 d . . . . .
C004 C 0.50290(16) 0.2482(2) 0.50273(11) 0.0264(4) Uani 1 1 d . . . . .
C005 C 0.44624(16) 0.2331(2) 0.42016(11) 0.0257(4) Uani 1 1 d . . . . .
C006 C 0.62814(16) 0.3421(2) 0.41728(11) 0.0267(5) Uani 1 1 d . . . . .
C007 C 0.32399(16) 0.1614(2) 0.40065(11) 0.0271(5) Uani 1 1 d . . . . .
C008 C 0.73664(16) 0.4117(2) 0.38350(11) 0.0276(5) Uani 1 1 d . . . . .
C009 C 0.44367(17) 0.2007(3) 0.57081(11) 0.0301(5) Uani 1 1 d . . . . .
H009 H 0.484018 0.212969 0.626529 0.036 Uiso 1 1 calc R . . . .
C00A C 0.26406(17) 0.1145(2) 0.46962(11) 0.0288(5) Uani 1 1 d . . . . .
C00B C 0.32531(18) 0.1361(3) 0.55301(12) 0.0316(5) Uani 1 1 d . . . . .
H00B H 0.282413 0.104576 0.597656 0.038 Uiso 1 1 calc R . . . .
C00C C 0.72109(18) 0.4918(3) 0.30520(12) 0.0340(5) Uani 1 1 d . . . . .
H00C H 0.640667 0.506592 0.274438 0.041 Uiso 1 1 calc R . . . .
C00D C 0.26125(16) 0.1378(3) 0.31896(11) 0.0308(5) Uani 1 1 d . . . . .
H00D H 0.300394 0.171547 0.272856 0.037 Uiso 1 1 calc R . . . .
C00E C 0.14280(17) 0.0416(3) 0.45337(12) 0.0345(5) Uani 1 1 d . . . . .
H00E H 0.101585 0.008449 0.498601 0.041 Uiso 1 1 calc R . . . .
C00F C 0.70770(17) 0.3633(3) 0.57348(11) 0.0329(5) Uani 1 1 d . . . . .
H00A H 0.666112 0.435714 0.611705 0.049 Uiso 1 1 calc GR . . . .
H00F H 0.776174 0.433765 0.556987 0.049 Uiso 1 1 calc GR . . . .
H00G H 0.739977 0.250958 0.601285 0.049 Uiso 1 1 calc GR . . . .
C00G C 0.14334(17) 0.0660(3) 0.30566(12) 0.0352(5) Uani 1 1 d . . . . .
H00H H 0.102229 0.048857 0.250414 0.042 Uiso 1 1 calc R . . . .
C00H C 0.82391(19) 0.5497(3) 0.27269(12) 0.0376(5) Uani 1 1 d . . . . .
H00I H 0.815438 0.604721 0.219226 0.045 Uiso 1 1 calc R . . . .
C00I C 0.08381(18) 0.0181(3) 0.37310(13) 0.0377(5) Uani 1 1 d . . . . .
H00J H 0.002451 -0.030742 0.363394 0.045 Uiso 1 1 calc R . . . .
C00J C 0.9395(2) 0.5262(3) 0.31920(13) 0.0419(6) Uani 1 1 d . . . . .
H00K H 1.011998 0.565030 0.298554 0.050 Uiso 1 1 calc R . . . .
C00K C 0.9469(2) 0.4452(3) 0.39624(14) 0.0450(6) Uani 1 1 d . . . . .
H00L H 1.026597 0.428541 0.427737 0.054 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
N2 C005 1.377(2) . ?
N2 C006 1.340(2) . ?
N1 C004 1.380(2) . ?
N1 C006 1.367(2) . ?
N1 C00F 1.462(2) . ?
N003 C008 1.346(2) . ?
N003 C00K 1.340(3) . ?
C004 C005 1.395(2) . ?
C004 C009 1.407(3) . ?
C005 C007 1.427(2) . ?
C006 C008 1.471(3) . ?
C007 C00A 1.423(3) . ?
C007 C00D 1.410(2) . ?
C008 C00C 1.389(3) . ?
C009 H009 0.9500 . ?
C009 C00B 1.368(3) . ?
C00A C00B 1.427(3) . ?
C00A C00E 1.417(3) . ?
C00B H00B 0.9500 . ?
C00C H00C 0.9500 . ?
C00C C00H 1.379(3) . ?
C00D H00D 0.9500 . ?
C00D C00G 1.379(3) . ?
C00E H00E 0.9500 . ?
C00E C00I 1.376(3) . ?
C00F H00A 0.9800 . ?
C00F H00F 0.9800 . ?
C00F H00G 0.9800 . ?
C00G H00H 0.9500 . ?
C00G C00I 1.401(3) . ?
C00H H00I 0.9500 . ?
C00H C00J 1.382(3) . ?
C00I H00J 0.9500 . ?
C00J H00K 0.9500 . ?
C00J C00K 1.378(3) . ?
C00K H00L 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
C006 N2 C005 104.63(14) . . ?
C004 N1 C00F 123.56(15) . . ?
C006 N1 C004 106.61(14) . . ?
C006 N1 C00F 129.72(15) . . ?
C00K N003 C008 116.97(18) . . ?
N1 C004 C005 105.80(16) . . ?
N1 C004 C009 131.10(16) . . ?
C005 C004 C009 123.10(17) . . ?
N2 C005 C004 110.41(16) . . ?
N2 C005 C007 129.01(16) . . ?
C004 C005 C007 120.57(17) . . ?
N2 C006 N1 112.55(16) . . ?
N2 C006 C008 121.31(16) . . ?
N1 C006 C008 126.13(16) . . ?
C00A C007 C005 116.17(16) . . ?
C00D C007 C005 124.14(17) . . ?
C00D C007 C00A 119.68(17) . . ?
N003 C008 C006 117.74(16) . . ?
N003 C008 C00C 122.58(17) . . ?
C00C C008 C006 119.63(16) . . ?
C004 C009 H009 121.6 . . ?
C00B C009 C004 116.89(17) . . ?
C00B C009 H009 121.6 . . ?
C007 C00A C00B 121.01(17) . . ?
C00E C00A C007 118.25(17) . . ?
C00E C00A C00B 120.73(17) . . ?
C009 C00B C00A 122.22(17) . . ?
C009 C00B H00B 118.9 . . ?
C00A C00B H00B 118.9 . . ?
C008 C00C H00C 120.4 . . ?
C00H C00C C008 119.14(18) . . ?
C00H C00C H00C 120.4 . . ?
C007 C00D H00D 119.8 . . ?
C00G C00D C007 120.35(17) . . ?
C00G C00D H00D 119.8 . . ?
C00A C00E H00E 119.5 . . ?
C00I C00E C00A 121.05(18) . . ?
C00I C00E H00E 119.5 . . ?
N1 C00F H00A 109.5 . . ?
N1 C00F H00F 109.5 . . ?
N1 C00F H00G 109.5 . . ?
H00A C00F H00F 109.5 . . ?
H00A C00F H00G 109.5 . . ?
H00F C00F H00G 109.5 . . ?
C00D C00G H00H 119.8 . . ?
C00D C00G C00I 120.43(18) . . ?
C00I C00G H00H 119.8 . . ?
C00C C00H H00I 120.6 . . ?
C00C C00H C00J 118.88(19) . . ?
C00J C00H H00I 120.6 . . ?
C00E C00I C00G 120.22(18) . . ?
C00E C00I H00J 119.9 . . ?
C00G C00I H00J 119.9 . . ?
C00H C00J H00K 120.8 . . ?
C00K C00J C00H 118.34(19) . . ?
C00K C00J H00K 120.8 . . ?
N003 C00K C00J 124.1(2) . . ?
N003 C00K H00L 118.0 . . ?
C00J C00K H00L 118.0 . . ?

_olex2_submission_original_sample_id HM-430A
_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane, petroleum ether'
_chemical_compound_source        synthetic
_chemical_properties_physical    Heat-sensitive,Light-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_K_101_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2025275'
loop_
_audit_author_name
_audit_author_address
'Ranjan Jana'
;CSIR Indian Institute of Chemical Biology
India
;
_audit_update_record             
;
2020-08-25 deposited with the CCDC.	2022-04-14 downloaded from the CCDC.
;
_audit_creation_date             2019-08-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_chemical_formula_moiety         'C23 H17 N3'
_chemical_formula_sum            'C23 H17 N3'
_chemical_formula_weight         335.41
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.01920 0.00962 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.03256 0.01839 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2ybc (x-z,y,z)'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x+1/2,y+1/2,-z+1/2
3 -x,-y,-z
4 x-1/2,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   11.8246(5)
_cell_length_b                   8.7668(4)
_cell_length_c                   16.2183(7)
_cell_angle_alpha                90
_cell_angle_beta                 90.457(2)
_cell_angle_gamma                90
_cell_volume                     1681.20(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7005
_cell_measurement_temperature    298
_cell_measurement_theta_max      66.522
_cell_measurement_theta_min      5.455
_exptl_absorpt_coefficient_mu    0.618
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.5796
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1419 before and 0.0939 after correction. The Ratio of minimum to maximum transmission is 0.7699. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            white
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.3251
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             706.0166
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.28
_diffrn_reflns_av_R_equivalents  0.0772
_diffrn_reflns_av_unetI/netI     0.0536
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            16494
_diffrn_reflns_theta_full        66.6097
_diffrn_reflns_theta_max         66.61
_diffrn_reflns_theta_min         5.46
_diffrn_ambient_temperature      298
_diffrn_measured_fraction_theta_full 0.9875
_diffrn_measured_fraction_theta_max 0.9875
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              11
_reflns_limit_h_min              -14
_reflns_limit_k_max              10
_reflns_limit_k_min              0
_reflns_limit_l_max              19
_reflns_limit_l_min              -10
_reflns_number_gt                2724
_reflns_number_total             2930
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_refine_diff_density_max         0.2797
_refine_diff_density_min         -0.3376
_refine_diff_density_rms         0.0865
_refine_ls_d_res_high            0.8399
_refine_ls_d_res_low             8.1089
_refine_ls_goodness_of_fit_ref   1.0730
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    33
_refine_ls_number_parameters     235
_refine_ls_number_reflns         2930
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0627
_refine_ls_R_factor_gt           0.0584
_refine_ls_restrained_S_all      1.0730
_refine_ls_shift/su_max          0.0010
_refine_ls_shift/su_mean         0.0003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0633P)²+1.2123P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1416
_refine_ls_wR_factor_ref         0.1448
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00D(H00c,H00d)
2.b Aromatic/amide H refined with riding coordinates:
 C009(H009), C00I(H00I), C00H(H00H), C00K(H00K), C00B(H00B), C00N(H00N),
 C00A(H00A), C00F(H00F), C00G(H00G), C00L(H00L), C00J(H00J), C00O(H00O),
 C00Q(H00Q), C00P(H00P), C00M(H00M)
;
_atom_sites_solution_primary     direct
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_refinement_flags_posn
N001 N 0.47945(13) 0.53079(18) 0.62986(10) 0.0210(4) Uani 1.000000 .
N002 N 0.37561(13) 0.70720(19) 0.56309(10) 0.0214(4) Uani 1.000000 .
N003 N 0.67708(13) 0.6388(2) 0.53905(11) 0.0255(4) Uani 1.000000 .
C004 C 0.30684(16) 0.6241(2) 0.61478(12) 0.0203(4) Uani 1.000000 .
C005 C 0.18824(16) 0.6390(2) 0.62876(12) 0.0205(4) Uani 1.000000 .
C006 C 0.14013(16) 0.5358(2) 0.68628(13) 0.0221(4) Uani 1.000000 .
C007 C 0.62402(16) 0.5106(2) 0.74188(13) 0.0212(4) Uani 1.000000 .
C008 C 0.36973(16) 0.5150(2) 0.65666(12) 0.0203(4) Uani 1.000000 .
C009 C 0.32264(17) 0.4138(2) 0.71467(12) 0.0224(4) Uani 1.000000 .
C00A C 0.57123(16) 0.6242(2) 0.78708(13) 0.0237(5) Uani 1.000000 .
C00B C 0.72273(17) 0.6215(2) 0.88743(13) 0.0270(5) Uani 1.000000 .
C00C C 0.57625(16) 0.7065(2) 0.52727(12) 0.0215(4) Uani 1.000000 .
C00D C 0.57377(16) 0.4420(2) 0.66393(13) 0.0225(5) Uani 1.000000 .
C00E C 0.47796(16) 0.6485(2) 0.57337(12) 0.0207(4) Uani 1.000000 .
C00F C 0.11956(16) 0.7516(2) 0.59125(13) 0.0236(5) Uani 1.000000 .
C00G C 0.00655(16) 0.7603(2) 0.60914(13) 0.0263(5) Uani 1.000000 .
C00H C 0.72620(16) 0.4515(2) 0.77109(13) 0.0255(5) Uani 1.000000 .
C00I C 0.20948(17) 0.4250(2) 0.72801(13) 0.0240(5) Uani 1.000000 .
C00J C 0.02325(17) 0.5470(2) 0.70247(13) 0.0251(5) Uani 1.000000 .
C00K C 0.77443(17) 0.5069(3) 0.84323(13) 0.0275(5) Uani 1.000000 .
C00L C -0.04277(17) 0.6561(2) 0.66433(14) 0.0276(5) Uani 1.000000 .
C00M C 0.56063(17) 0.8275(2) 0.47290(13) 0.0255(5) Uani 1.000000 .
C00N C 0.62034(17) 0.6798(2) 0.85959(14) 0.0273(5) Uani 1.000000 .
C00O C 0.76417(17) 0.6938(3) 0.49567(14) 0.0283(5) Uani 1.000000 .
C00P C 0.65242(18) 0.8847(2) 0.43105(14) 0.0299(5) Uani 1.000000 .
C00Q C 0.75677(18) 0.8156(3) 0.44261(14) 0.0300(5) Uani 1.000000 .
H009 H 0.36696(17) 0.3426(2) 0.74255(12) 0.0268(5) Uiso 1.000000 R
H00I H 0.17593(17) 0.3588(2) 0.76537(13) 0.0288(5) Uiso 1.000000 R
H00H H 0.76224(16) 0.3744(2) 0.74197(13) 0.0306(6) Uiso 1.000000 R
H00K H 0.84255(17) 0.4664(3) 0.86210(13) 0.0330(6) Uiso 1.000000 R
H00B H 0.75617(17) 0.6591(2) 0.93536(13) 0.0324(6) Uiso 1.000000 R
H00N H 0.58432(17) 0.7562(2) 0.88931(14) 0.0328(6) Uiso 1.000000 R
H00A H 0.50245(16) 0.6637(2) 0.76884(13) 0.0284(5) Uiso 1.000000 R
H00F H 0.15113(16) 0.8202(2) 0.55424(13) 0.0283(5) Uiso 1.000000 R
H00G H -0.03783(16) 0.8355(2) 0.58464(13) 0.0316(6) Uiso 1.000000 R
H00L H -0.11984(17) 0.6609(2) 0.67502(14) 0.0331(6) Uiso 1.000000 R
H00J H -0.00973(17) 0.4797(2) 0.73949(13) 0.0301(6) Uiso 1.000000 R
H00O H 0.83406(17) 0.6463(3) 0.50191(14) 0.0340(6) Uiso 1.000000 R
H00Q H 0.82031(18) 0.8509(3) 0.41509(14) 0.0360(6) Uiso 1.000000 R
H00P H 0.64448(18) 0.9678(2) 0.39584(14) 0.0359(6) Uiso 1.000000 R
H00M H 0.48912(17) 0.8694(2) 0.46487(13) 0.0306(6) Uiso 1.000000 R
H00c H 0.54758(16) 0.3396(2) 0.67588(13) 0.0270(5) Uiso 1.000000 R
H00d H 0.63249(16) 0.4343(2) 0.62272(13) 0.0270(5) Uiso 1.000000 R


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
N001 C008 1.379(2) . ?
N001 C00D 1.465(2) . ?
N001 C00E 1.380(3) . ?
N002 C004 1.381(3) . ?
N002 C00E 1.324(2) . ?
N003 C00C 1.344(3) . ?
N003 C00O 1.341(3) . ?
C004 C005 1.428(3) . ?
C004 C008 1.386(3) . ?
C005 C006 1.422(3) . ?
C005 C00F 1.413(3) . ?
C006 C00I 1.437(3) . ?
C006 C00J 1.412(3) . ?
C007 C00A 1.388(3) . ?
C007 C00D 1.517(3) . ?
C007 C00H 1.394(3) . ?
C008 C009 1.411(3) . ?
C009 C00I 1.361(3) . ?
C009 H009 0.9300 . ?
C00A C00N 1.395(3) . ?
C00A H00A 0.9300 . ?
C00B C00K 1.379(3) . ?
C00B C00N 1.387(3) . ?
C00B H00B 0.9300 . ?
C00C C00E 1.477(3) . ?
C00C C00M 1.391(3) . ?
C00D H00c 0.9700 . ?
C00D H00d 0.9700 . ?
C00F C00G 1.372(3) . ?
C00F H00F 0.9300 . ?
C00G C00L 1.408(3) . ?
C00G H00G 0.9300 . ?
C00H C00K 1.385(3) . ?
C00H H00H 0.9300 . ?
C00I H00I 0.9300 . ?
C00J C00L 1.378(3) . ?
C00J H00J 0.9300 . ?
C00K H00K 0.9300 . ?
C00L H00L 0.9300 . ?
C00M C00P 1.379(3) . ?
C00M H00M 0.9300 . ?
C00N H00N 0.9300 . ?
C00O C00Q 1.374(3) . ?
C00O H00O 0.9300 . ?
C00P C00Q 1.386(3) . ?
C00P H00P 0.9300 . ?
C00Q H00Q 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C00D N001 C008 122.90(16) . . ?
C00E N001 C008 106.11(16) . . ?
C00E N001 C00D 130.81(16) . . ?
C00E N002 C004 105.10(16) . . ?
C00O N003 C00C 116.81(19) . . ?
C005 C004 N002 129.17(18) . . ?
C008 C004 N002 110.21(16) . . ?
C008 C004 C005 120.62(18) . . ?
C006 C005 C004 116.36(18) . . ?
C00F C005 C004 123.89(18) . . ?
C00F C005 C006 119.72(18) . . ?
C00I C006 C005 120.63(18) . . ?
C00J C006 C005 118.34(18) . . ?
C00J C006 C00I 121.02(19) . . ?
C00D C007 C00A 123.35(17) . . ?
C00H C007 C00A 118.64(19) . . ?
C00H C007 C00D 117.96(18) . . ?
C004 C008 N001 106.18(17) . . ?
C009 C008 N001 130.61(18) . . ?
C009 C008 C004 123.20(18) . . ?
C00I C009 C008 117.02(18) . . ?
H009 C009 C008 121.49(11) . . ?
H009 C009 C00I 121.49(12) . . ?
C00N C00A C007 120.65(19) . . ?
H00A C00A C007 119.67(12) . . ?
H00A C00A C00N 119.67(12) . . ?
C00N C00B C00K 119.3(2) . . ?
H00B C00B C00K 120.37(12) . . ?
H00B C00B C00N 120.37(13) . . ?
C00E C00C N003 118.49(18) . . ?
C00M C00C N003 122.67(18) . . ?
C00M C00C C00E 118.83(18) . . ?
C007 C00D N001 113.32(16) . . ?
H00c C00D N001 108.91(10) . . ?
H00c C00D C007 108.91(11) . . ?
H00d C00D N001 108.91(10) . . ?
H00d C00D C007 108.91(10) . . ?
H00d C00D H00c 107.7 . . ?
N002 C00E N001 112.40(17) . . ?
C00C C00E N001 125.97(17) . . ?
C00C C00E N002 121.63(18) . . ?
C00G C00F C005 120.34(19) . . ?
H00F C00F C005 119.83(11) . . ?
H00F C00F C00G 119.83(13) . . ?
C00L C00G C00F 120.51(19) . . ?
H00G C00G C00F 119.75(13) . . ?
H00G C00G C00L 119.75(12) . . ?
C00K C00H C007 120.44(19) . . ?
H00H C00H C007 119.78(12) . . ?
H00H C00H C00K 119.78(12) . . ?
C009 C00I C006 122.16(19) . . ?
H00I C00I C006 118.92(11) . . ?
H00I C00I C009 118.92(12) . . ?
C00L C00J C006 121.11(19) . . ?
H00J C00J C006 119.45(12) . . ?
H00J C00J C00L 119.45(12) . . ?
C00H C00K C00B 120.86(19) . . ?
H00K C00K C00B 119.57(12) . . ?
H00K C00K C00H 119.57(12) . . ?
C00J C00L C00G 119.96(18) . . ?
H00L C00L C00G 120.02(12) . . ?
H00L C00L C00J 120.02(12) . . ?
C00P C00M C00C 119.2(2) . . ?
H00M C00M C00C 120.39(12) . . ?
H00M C00M C00P 120.39(13) . . ?
C00B C00N C00A 120.1(2) . . ?
H00N C00N C00A 119.93(12) . . ?
H00N C00N C00B 119.93(13) . . ?
C00Q C00O N003 124.2(2) . . ?
H00O C00O N003 117.89(12) . . ?
H00O C00O C00Q 117.89(12) . . ?
C00Q C00P C00M 118.5(2) . . ?
H00P C00P C00M 120.73(13) . . ?
H00P C00P C00Q 120.73(13) . . ?
C00P C00Q C00O 118.5(2) . . ?
H00Q C00Q C00O 120.76(12) . . ?
H00Q C00Q C00P 120.76(13) . . ?


_olex2_submission_special_instructions 'No special instructions were received'
_chemical_name_common            
3-benzyl-2-(pyridin-2-yl)-3H-naphtho[1,2-d]imidazole
_chemical_melting_point          414
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethne, petroleum ether'
_chemical_compound_source        synthetic
_chemical_properties_physical    Light-sensitive
