#------------------------------------------------------------------------------
#$Date: 2023-06-05 06:35:22 +0300 (Mon, 05 Jun 2023) $
#$Revision: 284174 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/15/7131555.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7131555
loop_
_publ_author_name
'Begam, Hasina Mamataj'
'Pradhan, Kangkan'
'Varalaxmi, Kasarla'
'Jana, Ranjan'
_publ_section_title
;
 An HFIP-assisted, cobalt-catalyzed three-component electrophilic C-H
 amination/cyclization/directing group removal cascade to
 naphtho[1,2-d]imidazoles.
;
_journal_issue                   37
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              5595
_journal_page_last               5598
_journal_paper_doi               10.1039/d3cc00749a
_journal_volume                  59
_journal_year                    2023
_chemical_formula_moiety         'C17 H18 N2'
_chemical_formula_sum            'C17 H18 N2'
_chemical_formula_weight         250.33
_chemical_name_systematic        monoclinic
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-05-11
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2022-11-21 deposited with the CCDC.	2023-04-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.428(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.2417(9)
_cell_length_b                   12.7619(9)
_cell_length_c                   7.8090(5)
_cell_measurement_reflns_used    9876
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      72.48
_cell_measurement_theta_min      3.46
_cell_volume                     1301.81(15)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100.00
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Bruker APEX-III 8D VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0811
_diffrn_reflns_av_unetI/netI     0.0436
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            25331
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.480
_diffrn_reflns_theta_min         4.844
_diffrn_source_current           1.2
_diffrn_source_power             0.06
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.580
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.3271
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1735 before and 0.1122 after correction.
The Ratio of minimum to maximum transmission is 0.4340.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_description       needle
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.464
_refine_diff_density_min         -0.369
_refine_diff_density_rms         0.075
_refine_ls_extinction_coef       0.062(7)
_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   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2532
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0699
_refine_ls_R_factor_gt           0.0672
_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)+(0.1260P)²+0.3059P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1766
_refine_ls_wR_factor_ref         0.1802
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2356
_reflns_number_total             2532
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3cc00749a2.cif
_cod_data_source_block           f
_cod_depositor_comments
'Adding full bibliography for 7131554--7131555.cif.'
_cod_database_code               7131555
_shelx_shelxl_version_number     2018/3
_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.
;
_shelx_estimated_absorpt_t_max   0.989
_shelx_estimated_absorpt_t_min   0.918
_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:
 C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C15(H15A,H15B), C13(H13A,H13B), C14(H14A,H14B), C16(H16A,H16B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C11(H11), C8(H8), C4(H4), C7(H7), C6(H6), C5(H5)
;
_olex2_submission_special_instructions 'No special instructions were received'
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'
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
N1 N 0.45845(10) 0.55020(10) 0.27388(16) 0.0255(4) Uani 1 1 d . . . . .
N2 N 0.59135(10) 0.45676(10) 0.20955(16) 0.0276(4) Uani 1 1 d . . . . .
C2 C 0.54604(12) 0.60451(12) 0.34301(18) 0.0249(4) Uani 1 1 d . . . . .
C1 C 0.62703(12) 0.54629(11) 0.30016(18) 0.0245(4) Uani 1 1 d . . . . .
C3 C 0.56131(13) 0.69782(12) 0.44223(19) 0.0277(4) Uani 1 1 d . . . . .
H3 H 0.505376 0.735373 0.474454 0.033 Uiso 1 1 calc R U . . .
C9 C 0.72980(12) 0.58109(12) 0.34720(18) 0.0247(4) Uani 1 1 d . . . . .
C10 C 0.74551(13) 0.67639(12) 0.44230(19) 0.0277(4) Uani 1 1 d . . . . .
C11 C 0.49123(13) 0.46340(12) 0.1986(2) 0.0283(4) Uani 1 1 d . . . . .
H11 H 0.445708 0.411759 0.142573 0.034 Uiso 1 1 calc R U . . .
C12 C 0.35170(12) 0.58292(12) 0.27555(19) 0.0260(4) Uani 1 1 d . . . . .
H12 H 0.343407 0.596303 0.398658 0.031 Uiso 1 1 calc R U . . .
C17 C 0.32644(13) 0.68450(12) 0.1721(2) 0.0273(4) Uani 1 1 d . . . . .
H17A H 0.374828 0.740322 0.220115 0.033 Uiso 1 1 calc R U . . .
H17B H 0.333984 0.673011 0.049411 0.033 Uiso 1 1 calc R U . . .
C8 C 0.81419(13) 0.52677(13) 0.30173(19) 0.0281(4) Uani 1 1 d . . . . .
H8 H 0.803677 0.462941 0.238719 0.034 Uiso 1 1 calc R U . . .
C4 C 0.65993(13) 0.73153(12) 0.48963(19) 0.0293(4) Uani 1 1 d . . . . .
H4 H 0.672169 0.793813 0.556421 0.035 Uiso 1 1 calc R U . . .
C15 C 0.13899(13) 0.63326(13) 0.1186(2) 0.0314(4) Uani 1 1 d . . . . .
H15A H 0.136139 0.622820 -0.007751 0.038 Uiso 1 1 calc R U . . .
H15B H 0.070263 0.655640 0.138429 0.038 Uiso 1 1 calc R U . . .
C13 C 0.27735(13) 0.49693(12) 0.2035(2) 0.0290(4) Uani 1 1 d . . . . .
H13A H 0.294018 0.431760 0.270940 0.035 Uiso 1 1 calc R U . . .
H13B H 0.284083 0.482639 0.081233 0.035 Uiso 1 1 calc R U . . .
C7 C 0.91156(13) 0.56560(14) 0.3480(2) 0.0329(4) Uani 1 1 d . . . . .
H7 H 0.968005 0.528835 0.316020 0.040 Uiso 1 1 calc R U . . .
C14 C 0.16720(13) 0.52982(14) 0.2131(2) 0.0335(4) Uani 1 1 d . . . . .
H14A H 0.119679 0.474339 0.160793 0.040 Uiso 1 1 calc R U . . .
H14B H 0.159132 0.537290 0.336369 0.040 Uiso 1 1 calc R U . . .
C16 C 0.21665(13) 0.71882(13) 0.1816(2) 0.0300(4) Uani 1 1 d . . . . .
H16A H 0.211485 0.737099 0.303053 0.036 Uiso 1 1 calc R U . . .
H16B H 0.200194 0.782341 0.109645 0.036 Uiso 1 1 calc R U . . .
C6 C 0.92814(14) 0.65964(15) 0.4427(2) 0.0366(5) Uani 1 1 d . . . . .
H6 H 0.995738 0.685945 0.474341 0.044 Uiso 1 1 calc R U . . .
C5 C 0.84728(14) 0.71355(14) 0.4897(2) 0.0336(4) Uani 1 1 d . . . . .
H5 H 0.859559 0.776509 0.554667 0.040 Uiso 1 1 calc R U . . .
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C12 126.72(12) . . ?
C11 N1 C2 105.71(13) . . ?
C11 N1 C12 127.51(14) . . ?
C11 N2 C1 103.63(13) . . ?
N1 C2 C1 105.60(13) . . ?
N1 C2 C3 132.08(14) . . ?
C1 C2 C3 122.29(15) . . ?
N2 C1 C2 110.60(14) . . ?
N2 C1 C9 128.43(14) . . ?
C2 C1 C9 120.97(14) . . ?
C2 C3 H3 121.4 . . ?
C4 C3 C2 117.18(14) . . ?
C4 C3 H3 121.4 . . ?
C1 C9 C10 117.00(14) . . ?
C8 C9 C1 123.12(14) . . ?
C8 C9 C10 119.87(15) . . ?
C9 C10 C4 120.02(15) . . ?
C5 C10 C9 118.24(15) . . ?
C5 C10 C4 121.73(15) . . ?
N1 C11 H11 122.8 . . ?
N2 C11 N1 114.45(14) . . ?
N2 C11 H11 122.8 . . ?
N1 C12 H12 108.2 . . ?
N1 C12 C17 111.14(12) . . ?
N1 C12 C13 110.84(12) . . ?
C17 C12 H12 108.2 . . ?
C13 C12 H12 108.2 . . ?
C13 C12 C17 110.04(13) . . ?
C12 C17 H17A 109.7 . . ?
C12 C17 H17B 109.7 . . ?
H17A C17 H17B 108.2 . . ?
C16 C17 C12 110.03(13) . . ?
C16 C17 H17A 109.7 . . ?
C16 C17 H17B 109.7 . . ?
C9 C8 H8 119.8 . . ?
C7 C8 C9 120.34(15) . . ?
C7 C8 H8 119.8 . . ?
C3 C4 C10 122.44(14) . . ?
C3 C4 H4 118.8 . . ?
C10 C4 H4 118.8 . . ?
H15A C15 H15B 108.0 . . ?
C14 C15 H15A 109.4 . . ?
C14 C15 H15B 109.4 . . ?
C16 C15 H15A 109.4 . . ?
C16 C15 H15B 109.4 . . ?
C16 C15 C14 111.34(14) . . ?
C12 C13 H13A 109.6 . . ?
C12 C13 H13B 109.6 . . ?
C12 C13 C14 110.39(13) . . ?
H13A C13 H13B 108.1 . . ?
C14 C13 H13A 109.6 . . ?
C14 C13 H13B 109.6 . . ?
C8 C7 H7 119.8 . . ?
C8 C7 C6 120.32(16) . . ?
C6 C7 H7 119.8 . . ?
C15 C14 C13 111.84(13) . . ?
C15 C14 H14A 109.2 . . ?
C15 C14 H14B 109.2 . . ?
C13 C14 H14A 109.2 . . ?
C13 C14 H14B 109.2 . . ?
H14A C14 H14B 107.9 . . ?
C17 C16 H16A 109.2 . . ?
C17 C16 H16B 109.2 . . ?
C15 C16 C17 112.01(13) . . ?
C15 C16 H16A 109.2 . . ?
C15 C16 H16B 109.2 . . ?
H16A C16 H16B 107.9 . . ?
C7 C6 H6 119.8 . . ?
C5 C6 C7 120.43(16) . . ?
C5 C6 H6 119.8 . . ?
C10 C5 H5 119.6 . . ?
C6 C5 C10 120.79(16) . . ?
C6 C5 H5 119.6 . . ?
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 C2 1.383(2) . ?
N1 C11 1.358(2) . ?
N1 C12 1.4760(19) . ?
N2 C1 1.3856(19) . ?
N2 C11 1.317(2) . ?
C2 C1 1.390(2) . ?
C2 C3 1.417(2) . ?
C1 C9 1.421(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.367(2) . ?
C9 C10 1.422(2) . ?
C9 C8 1.409(2) . ?
C10 C4 1.433(2) . ?
C10 C5 1.419(2) . ?
C11 H11 0.9500 . ?
C12 H12 1.0000 . ?
C12 C17 1.535(2) . ?
C12 C13 1.519(2) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C16 1.532(2) . ?
C8 H8 0.9500 . ?
C8 C7 1.373(2) . ?
C4 H4 0.9500 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C14 1.529(2) . ?
C15 C16 1.525(2) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.531(2) . ?
C7 H7 0.9500 . ?
C7 C6 1.408(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C6 H6 0.9500 . ?
C6 C5 1.372(3) . ?
C5 H5 0.9500 . ?
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
N1 C2 C1 N2 -1.16(16) . . . . ?
N1 C2 C1 C9 178.24(12) . . . . ?
N1 C2 C3 C4 -179.41(14) . . . . ?
N1 C12 C17 C16 -177.90(12) . . . . ?
N1 C12 C13 C14 177.54(12) . . . . ?
N2 C1 C9 C10 -179.51(13) . . . . ?
N2 C1 C9 C8 1.5(2) . . . . ?
C2 N1 C11 N2 -1.00(18) . . . . ?
C2 N1 C12 C17 63.21(18) . . . . ?
C2 N1 C12 C13 -174.08(13) . . . . ?
C2 C1 C9 C10 1.2(2) . . . . ?
C2 C1 C9 C8 -177.79(13) . . . . ?
C2 C3 C4 C10 0.1(2) . . . . ?
C1 N2 C11 N1 0.28(17) . . . . ?
C1 C2 C3 C4 2.5(2) . . . . ?
C1 C9 C10 C4 1.3(2) . . . . ?
C1 C9 C10 C5 -179.44(13) . . . . ?
C1 C9 C8 C7 178.66(13) . . . . ?
C3 C2 C1 N2 177.37(13) . . . . ?
C3 C2 C1 C9 -3.2(2) . . . . ?
C9 C10 C4 C3 -2.0(2) . . . . ?
C9 C10 C5 C6 0.9(2) . . . . ?
C9 C8 C7 C6 0.6(2) . . . . ?
C10 C9 C8 C7 -0.3(2) . . . . ?
C11 N1 C2 C1 1.25(15) . . . . ?
C11 N1 C2 C3 -177.07(15) . . . . ?
C11 N1 C12 C17 -113.80(16) . . . . ?
C11 N1 C12 C13 8.9(2) . . . . ?
C11 N2 C1 C2 0.57(16) . . . . ?
C11 N2 C1 C9 -178.78(15) . . . . ?
C12 N1 C2 C1 -176.28(13) . . . . ?
C12 N1 C2 C3 5.4(2) . . . . ?
C12 N1 C11 N2 176.51(13) . . . . ?
C12 C17 C16 C15 -56.10(16) . . . . ?
C12 C13 C14 C15 56.36(18) . . . . ?
C17 C12 C13 C14 -59.12(16) . . . . ?
C8 C9 C10 C4 -179.64(13) . . . . ?
C8 C9 C10 C5 -0.4(2) . . . . ?
C8 C7 C6 C5 -0.1(2) . . . . ?
C4 C10 C5 C6 -179.87(14) . . . . ?
C13 C12 C17 C16 58.94(16) . . . . ?
C7 C6 C5 C10 -0.7(3) . . . . ?
C14 C15 C16 C17 53.10(17) . . . . ?
C16 C15 C14 C13 -52.98(18) . . . . ?
C5 C10 C4 C3 178.75(14) . . . . ?
