#------------------------------------------------------------------------------
#$Date: 2025-08-20 12:41:31 +0300 (Wed, 20 Aug 2025) $
#$Revision: 301828 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/02/4030202.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_4030202
loop_
_publ_author_name
'Zhang, Lei'
'Zheng, Liyao'
'Guo, Biao'
'Hua, Ruimao'
_publ_section_title
;
 One-pot synthesis of multisubstituted 2-aminoquinolines from annulation
 of 1-aryl tetrazoles with internal alkynes via double C-H activation and
 denitrogenation.
;
_journal_issue                   23
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              11541
_journal_page_last               11548
_journal_paper_doi               10.1021/jo502192b
_journal_volume                  79
_journal_year                    2014
_chemical_formula_moiety         'C21 H13 Cl N4'
_chemical_formula_sum            'C21 H13 Cl N4'
_chemical_formula_weight         356.80
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_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                 124.311(18)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   19.728(5)
_cell_length_b                   12.427(6)
_cell_length_c                   17.190(5)
_cell_measurement_reflns_used    47
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      12.49
_cell_measurement_theta_min      5.81
_cell_volume                     3481(2)
_computing_cell_refinement       'XSCANS (Bruker, 1997)'
_computing_data_collection       'XSCANS (Bruker, 1997)'
_computing_data_reduction        'XSCANS (Bruker, 1997)'
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  'SHELXTL (Bruker, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0469
_diffrn_reflns_av_sigmaI/netI    0.0368
_diffrn_reflns_limit_h_max       1
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            3897
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         2.06
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.231
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1472
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.40
_refine_diff_density_max         0.189
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       0.00092(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3242
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0779
_refine_ls_R_factor_gt           0.0463
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0010P)²+4.5000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0820
_refine_ls_wR_factor_ref         0.0956
_reflns_number_gt                2226
_reflns_number_total             3242
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            jo502192b_si_002.cif
_cod_data_source_block           3j'
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/home/saulius/struct/COD-crude-data--automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2935 2014-11-11 08:27:57Z andrius 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 

 Adding full bibliography for 4030202--4030203.cif.
;
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               4030202
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Cl1 Cl 1.16053(4) 0.55938(8) 1.05049(5) 0.0854(3) Uani 1 1 d .
N1 N 0.89731(13) 0.29505(16) 0.75574(14) 0.0515(5) Uani 1 1 d .
N2 N 0.89630(16) 0.18598(17) 0.74786(17) 0.0660(6) Uani 1 1 d .
N3 N 0.82371(16) 0.16345(18) 0.67488(18) 0.0725(7) Uani 1 1 d .
N4 N 0.77724(14) 0.25218(17) 0.63473(15) 0.0618(6) Uani 1 1 d .
C1 C 0.82427(14) 0.33407(19) 0.68636(16) 0.0474(6) Uani 1 1 d .
C2 C 0.80858(14) 0.44747(18) 0.67908(16) 0.0444(5) Uani 1 1 d .
C3 C 0.87090(13) 0.51169(18) 0.74482(15) 0.0436(5) Uani 1 1 d .
C4 C 0.94845(14) 0.46649(19) 0.81992(16) 0.0457(5) Uani 1 1 d .
C5 C 0.96233(14) 0.35500(19) 0.82540(16) 0.0491(6) Uani 1 1 d .
C6 C 1.03551(16) 0.3083(2) 0.89458(18) 0.0605(7) Uani 1 1 d .
H6 H 1.0428 0.2344 0.8944 0.073 Uiso 1 1 calc R
C7 C 1.09689(16) 0.3706(3) 0.96292(19) 0.0645(8) Uani 1 1 d .
H7 H 1.1465 0.3400 1.0101 0.077 Uiso 1 1 calc R
C8 C 1.08436(15) 0.4807(2) 0.96113(17) 0.0599(7) Uani 1 1 d .
C9 C 1.01303(14) 0.5286(2) 0.89099(16) 0.0536(6) Uani 1 1 d .
H9 H 1.0075 0.6030 0.8906 0.064 Uiso 1 1 calc R
C10 C 0.72580(13) 0.48547(19) 0.60389(16) 0.0469(6) Uani 1 1 d .
C11 C 0.68889(15) 0.4513(2) 0.51209(17) 0.0542(6) Uani 1 1 d .
H11 H 0.7169 0.4051 0.4970 0.065 Uiso 1 1 calc R
C12 C 0.61104(16) 0.4848(2) 0.44288(19) 0.0654(7) Uani 1 1 d .
H12 H 0.5867 0.4616 0.3812 0.078 Uiso 1 1 calc R
C13 C 0.56928(16) 0.5524(3) 0.4647(2) 0.0726(8) Uani 1 1 d .
H13 H 0.5167 0.5754 0.4178 0.087 Uiso 1 1 calc R
C14 C 0.60494(17) 0.5862(2) 0.5553(2) 0.0717(8) Uani 1 1 d .
H14 H 0.5761 0.6315 0.5700 0.086 Uiso 1 1 calc R
C15 C 0.68286(15) 0.5539(2) 0.62506(19) 0.0569(6) Uani 1 1 d .
H15 H 0.7068 0.5779 0.6865 0.068 Uiso 1 1 calc R
C16 C 0.86274(13) 0.63115(18) 0.73853(16) 0.0447(5) Uani 1 1 d .
C17 C 0.85334(16) 0.6838(2) 0.66285(19) 0.0604(7) Uani 1 1 d .
H17 H 0.8513 0.6449 0.6153 0.072 Uiso 1 1 calc R
C18 C 0.84691(19) 0.7948(2) 0.6573(2) 0.0800(9) Uani 1 1 d .
H18 H 0.8402 0.8304 0.6058 0.096 Uiso 1 1 calc R
C19 C 0.85045(18) 0.8522(2) 0.7272(3) 0.0782(9) Uani 1 1 d .
H19 H 0.8474 0.9269 0.7239 0.094 Uiso 1 1 calc R
C20 C 0.85834(17) 0.8005(2) 0.8013(2) 0.0700(8) Uani 1 1 d .
H20 H 0.8596 0.8397 0.8482 0.084 Uiso 1 1 calc R
C21 C 0.86446(16) 0.6901(2) 0.80730(19) 0.0595(7) Uani 1 1 d .
H21 H 0.8698 0.6551 0.8583 0.071 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'
N N 0.0061 0.0033 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1 N1 N2 108.9(2)
C1 N1 C5 125.8(2)
N2 N1 C5 125.3(2)
N3 N2 N1 104.9(2)
N2 N3 N4 112.4(2)
C1 N4 N3 105.5(2)
N4 C1 N1 108.3(2)
N4 C1 C2 131.4(2)
N1 C1 C2 120.3(2)
C3 C2 C1 117.0(2)
C3 C2 C10 125.0(2)
C1 C2 C10 118.0(2)
C2 C3 C4 121.2(2)
C2 C3 C16 120.8(2)
C4 C3 C16 117.9(2)
C9 C4 C5 116.0(2)
C9 C4 C3 123.3(2)
C5 C4 C3 120.7(2)
C6 C5 N1 122.1(2)
C6 C5 C4 122.9(2)
N1 C5 C4 115.1(2)
C7 C6 C5 119.8(3)
C7 C6 H6 120.1
C5 C6 H6 120.1
C6 C7 C8 118.8(2)
C6 C7 H7 120.6
C8 C7 H7 120.6
C9 C8 C7 122.0(3)
C9 C8 Cl1 119.0(2)
C7 C8 Cl1 119.0(2)
C8 C9 C4 120.4(2)
C8 C9 H9 119.8
C4 C9 H9 119.8
C11 C10 C15 118.8(2)
C11 C10 C2 120.8(2)
C15 C10 C2 120.3(2)
C12 C11 C10 120.6(3)
C12 C11 H11 119.7
C10 C11 H11 119.7
C13 C12 C11 120.1(3)
C13 C12 H12 120.0
C11 C12 H12 120.0
C14 C13 C12 119.9(3)
C14 C13 H13 120.0
C12 C13 H13 120.0
C13 C14 C15 120.6(3)
C13 C14 H14 119.7
C15 C14 H14 119.7
C14 C15 C10 120.0(3)
C14 C15 H15 120.0
C10 C15 H15 120.0
C17 C16 C21 119.1(2)
C17 C16 C3 119.7(2)
C21 C16 C3 121.3(2)
C16 C17 C18 119.9(3)
C16 C17 H17 120.1
C18 C17 H17 120.1
C19 C18 C17 120.3(3)
C19 C18 H18 119.9
C17 C18 H18 119.9
C20 C19 C18 120.1(3)
C20 C19 H19 120.0
C18 C19 H19 120.0
C19 C20 C21 120.2(3)
C19 C20 H20 119.9
C21 C20 H20 119.9
C16 C21 C20 120.5(3)
C16 C21 H21 119.7
C20 C21 H21 119.7
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C8 1.724(3)
N1 C1 1.340(3)
N1 N2 1.361(3)
N1 C5 1.379(3)
N2 N3 1.295(3)
N3 N4 1.349(3)
N4 C1 1.325(3)
C1 C2 1.433(3)
C2 C3 1.364(3)
C2 C10 1.477(3)
C3 C4 1.448(3)
C3 C16 1.491(3)
C4 C9 1.399(3)
C4 C5 1.405(3)
C5 C6 1.378(3)
C6 C7 1.357(4)
C6 H6 0.9300
C7 C8 1.388(4)
C7 H7 0.9300
C8 C9 1.370(3)
C9 H9 0.9300
C10 C11 1.380(3)
C10 C15 1.386(3)
C11 C12 1.374(3)
C11 H11 0.9300
C12 C13 1.368(4)
C12 H12 0.9300
C13 C14 1.365(4)
C13 H13 0.9300
C14 C15 1.372(4)
C14 H14 0.9300
C15 H15 0.9300
C16 C17 1.372(3)
C16 C21 1.375(3)
C17 C18 1.383(4)
C17 H17 0.9300
C18 C19 1.364(4)
C18 H18 0.9300
C19 C20 1.355(4)
C19 H19 0.9300
C20 C21 1.376(4)
C20 H20 0.9300
C21 H21 0.9300
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139093926
