#------------------------------------------------------------------------------
#$Date: 2025-08-20 11:41:31 +0200 (Wed 20 de Aug de 2025) $
#$Revision: 301828 $
#$URL: svn://www.crystallography.net/cod/cif/4/03/33/4033328.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_4033328
loop_
_publ_author_name
'Sau, Prasenjit'
'Rakshit, Amitava'
'Modi, Anju'
'Behera, Ahalya'
'Patel, Bhisma K.'
_publ_section_title
;
 Three Sequential C-N Bond Formations: tert-Butyl Nitrite as a N1 Synthon
 in a Three Component Reaction Leading to Imidazo[1,2-a]quinolines and
 Imidazo[2,1-a]isoquinolines.
;
_journal_issue                   2
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              1056
_journal_page_last               1064
_journal_paper_doi               10.1021/acs.joc.7b02815
_journal_volume                  83
_journal_year                    2018
_chemical_compound_source        Synthesis
_chemical_formula_moiety         'C17 H11 Cl N2'
_chemical_formula_sum            'C17 H11 Cl N2'
_chemical_formula_weight         278.73
_chemical_name_systematic        Unkown
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      29
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.3293(6)
_cell_length_b                   3.9877(2)
_cell_length_c                   26.5458(16)
_cell_measurement_reflns_used    3406
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.99
_cell_measurement_theta_min      3.30
_cell_volume                     1305.14(12)
_computing_cell_refinement       'CrysAlisPro, Agilent Technologies'
_computing_data_collection       'CrysAlisPro, Agilent Technologies'
_computing_data_reduction        'CrysAlisPro, Agilent Technologies'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'SuperNova, Single source at offset), Eos'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0174
_diffrn_reflns_av_sigmaI/netI    0.0301
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -2
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            2756
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         3.30
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.282
_exptl_absorpt_correction_T_max  0.972
_exptl_absorpt_correction_T_min  0.960
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            White
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Needle
_exptl_crystal_F_000             576
_exptl_crystal_recrystallization_method
'Ethylacetate and methanol solvent mixture'
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.137
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.03(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         1644
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.093
_refine_ls_R_factor_all          0.0444
_refine_ls_R_factor_gt           0.0344
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0372P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0725
_refine_ls_wR_factor_ref         0.0821
_reflns_number_gt                1412
_reflns_number_total             1644
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo7b02815_si_002.cif
_cod_data_source_block           exp_4037
_cod_depositor_comments          'Adding full bibliography for 4033328.cif.'
_cod_database_code               4033328
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y, z+1/2'
'x+1/2, -y, z'
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
Cl1 Cl 0.21057(9) 0.7845(3) 0.92698(4) 0.0863(4) Uani 1 1 d .
C5 C 0.6087(2) 0.6976(7) 0.58057(13) 0.0477(8) Uani 1 1 d .
C9 C 0.5193(2) 0.7585(6) 0.66219(12) 0.0418(7) Uani 1 1 d .
N2 N 0.44525(18) 0.8341(6) 0.69622(9) 0.0429(6) Uani 1 1 d .
C4 C 0.6092(3) 0.7561(8) 0.52871(14) 0.0559(9) Uani 1 1 d .
H4 H 0.6673 0.6811 0.5094 0.067 Uiso 1 1 calc R
N1 N 0.60693(17) 0.5956(6) 0.68429(10) 0.0476(7) Uani 1 1 d .
C7 C 0.6952(2) 0.5260(8) 0.60634(15) 0.0567(9) Uani 1 1 d .
H7 H 0.7533 0.4444 0.5877 0.068 Uiso 1 1 calc R
C12 C 0.4222(2) 0.7487(7) 0.78793(12) 0.0448(7) Uani 1 1 d .
C3 C 0.5254(3) 0.9223(9) 0.50588(14) 0.0615(9) Uani 1 1 d .
H3 H 0.5266 0.9568 0.4712 0.074 Uiso 1 1 calc R
C13 C 0.4567(2) 0.6106(8) 0.83330(13) 0.0551(8) Uani 1 1 d .
H13 H 0.5241 0.5061 0.8347 0.066 Uiso 1 1 calc R
C1 C 0.4359(2) 0.9893(8) 0.58536(11) 0.0474(8) Uani 1 1 d .
H1 H 0.3778 1.0682 0.6043 0.057 Uiso 1 1 calc R
C10 C 0.5857(2) 0.5744(7) 0.73459(13) 0.0507(8) Uani 1 1 d .
H10 H 0.6300 0.4817 0.7593 0.061 Uiso 1 1 calc R
C6 C 0.5204(2) 0.8194(7) 0.60900(12) 0.0421(7) Uani 1 1 d .
C11 C 0.4857(2) 0.7177(7) 0.74132(12) 0.0442(7) Uani 1 1 d .
C16 C 0.2570(3) 0.9215(8) 0.83013(12) 0.0539(8) Uani 1 1 d .
H16 H 0.1899 1.0276 0.8292 0.065 Uiso 1 1 calc R
C15 C 0.2932(3) 0.7760(8) 0.87382(14) 0.0558(8) Uani 1 1 d .
C14 C 0.3936(3) 0.6244(8) 0.87639(13) 0.0596(9) Uani 1 1 d .
H14 H 0.4185 0.5331 0.9065 0.072 Uiso 1 1 calc R
C2 C 0.4380(2) 1.0406(9) 0.53436(13) 0.0553(8) Uani 1 1 d .
H2 H 0.3814 1.1540 0.5187 0.066 Uiso 1 1 calc R
C8 C 0.6946(2) 0.4804(8) 0.65598(15) 0.0559(9) Uani 1 1 d .
H8 H 0.7523 0.3725 0.6717 0.067 Uiso 1 1 calc R
C17 C 0.3213(2) 0.9091(7) 0.78746(12) 0.0497(8) Uani 1 1 d .
H17 H 0.2970 1.0093 0.7579 0.060 Uiso 1 1 calc R
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'
Cl Cl 0.1484 0.1585 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C4 C5 C6 118.3(3)
C4 C5 C7 123.0(3)
C6 C5 C7 118.7(3)
N2 C9 N1 110.8(3)
N2 C9 C6 130.0(3)
N1 C9 C6 119.2(3)
C9 N2 C11 105.5(2)
C3 C4 C5 120.9(3)
C10 N1 C9 107.0(2)
C10 N1 C8 131.0(3)
C9 N1 C8 121.9(3)
C8 C7 C5 122.2(3)
C13 C12 C17 117.4(3)
C13 C12 C11 122.2(3)
C17 C12 C11 120.3(3)
C4 C3 C2 120.4(4)
C14 C13 C12 121.9(3)
C2 C1 C6 120.3(3)
N1 C10 C11 105.9(3)
C1 C6 C5 120.2(3)
C1 C6 C9 121.3(3)
C5 C6 C9 118.5(3)
C10 C11 N2 110.7(3)
C10 C11 C12 128.6(3)
N2 C11 C12 120.7(2)
C15 C16 C17 119.4(3)
C16 C15 C14 121.3(3)
C16 C15 Cl1 119.2(3)
C14 C15 Cl1 119.6(3)
C15 C14 C13 118.7(3)
C1 C2 C3 119.9(3)
C7 C8 N1 119.5(3)
C16 C17 C12 121.3(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C15 1.740(3)
C5 C4 1.396(4)
C5 C6 1.410(4)
C5 C7 1.440(4)
C9 N2 1.319(4)
C9 N1 1.390(3)
C9 C6 1.433(4)
N2 C11 1.378(4)
C4 C3 1.369(5)
N1 C10 1.363(4)
N1 C8 1.395(4)
C7 C8 1.330(5)
C12 C13 1.391(4)
C12 C17 1.399(4)
C12 C11 1.469(4)
C3 C2 1.398(4)
C13 C14 1.384(5)
C1 C2 1.369(4)
C1 C6 1.393(4)
C10 C11 1.370(4)
C16 C15 1.371(5)
C16 C17 1.384(4)
C15 C14 1.380(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 829290
