#------------------------------------------------------------------------------
#$Date: 2025-08-22 10:56:18 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301860 $
#$URL: svn://www.crystallography.net/cod/cif/7/12/41/7124153.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_7124153
loop_
_publ_author_name
'Kumar, Pradeep'
'Garg, Vineeta'
'Kumar, Manoj'
'Verma, Akhilesh K.'
_publ_section_title
;
 Rh(III)-Catalyzed Alkynylation: Synthesis of Functionalized Quinolines
 from Aminohydrazones
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC06205J
_journal_year                    2019
_chemical_formula_moiety         'C19 H16 N2'
_chemical_formula_sum            'C19 H16 N2'
_chemical_formula_weight         272.34
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2016/4
_audit_update_record
;
2017-12-16 deposited with the CCDC.    2019-09-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.933(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.0425(5)
_cell_length_b                   12.1560(7)
_cell_length_c                   14.5478(9)
_cell_measurement_reflns_used    2185
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      25.0
_cell_measurement_theta_min      3.4
_cell_volume                     1408.65(15)
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Xcalibur Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0599
_diffrn_reflns_av_unetI/netI     0.0637
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            14062
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.308
_diffrn_reflns_theta_min         2.557
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  0.9879
_exptl_absorpt_correction_T_min  0.9780
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_description       needle
_exptl_crystal_F_000             576.0
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.662
_refine_diff_density_min         -0.623
_refine_diff_density_rms         0.082
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.787
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         3509
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.787
_refine_ls_R_factor_all          0.1204
_refine_ls_R_factor_gt           0.0739
_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)+(0.1795P)²+2.8757P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2061
_refine_ls_wR_factor_ref         0.2498
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2258
_reflns_number_total             3511
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9cc06205j2.cif
_cod_data_source_block           shelx
_cod_database_code               7124153
_shelx_shelxl_version_number     2016/4
_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.
;
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
N1 N 0.6609(3) -0.12167(16) 0.80594(14) 0.0152(5) Uani 1 1 d . .
N2 N -0.0456(3) -0.1679(2) 1.00498(18) 0.0280(6) Uani 1 1 d . .
C7 C 0.2862(3) -0.0442(2) 0.91459(16) 0.0155(5) Uani 1 1 d . .
H7 H 0.231387 0.017216 0.933980 0.019 Uiso 1 1 calc R U
C3 C 0.3015(3) -0.2427(2) 0.89522(18) 0.0182(5) Uani 1 1 d . .
H3 H 0.255896 -0.312153 0.901675 0.022 Uiso 1 1 calc R U
C12 C 0.8836(3) -0.02068(19) 0.75084(16) 0.0143(5) Uani 1 1 d . .
C6 C 0.4349(3) -0.03084(19) 0.87417(16) 0.0142(5) Uani 1 1 d . .
C10 C 0.7279(3) -0.02375(19) 0.79558(16) 0.0144(5) Uani 1 1 d . .
C4 C 0.4460(3) -0.2309(2) 0.85657(18) 0.0172(5) Uani 1 1 d . .
H4 H 0.499176 -0.293115 0.837560 0.021 Uiso 1 1 calc R U
C9 C 0.6536(3) 0.07507(19) 0.82275(17) 0.0149(5) Uani 1 1 d . .
H9 H 0.704777 0.142102 0.813852 0.018 Uiso 1 1 calc R U
C17 C 0.9732(3) 0.0762(2) 0.74209(17) 0.0170(5) Uani 1 1 d . .
H17 H 0.939257 0.140835 0.768143 0.020 Uiso 1 1 calc R U
C14 C 1.0811(3) -0.1154(2) 0.66731(17) 0.0167(5) Uani 1 1 d . .
H14 H 1.117226 -0.180494 0.642929 0.020 Uiso 1 1 calc R U
C11 C 0.4266(3) 0.1770(2) 0.88858(18) 0.0181(5) Uani 1 1 d . .
H11A H 0.326612 0.159172 0.914601 0.027 Uiso 1 1 calc R U
H11B H 0.502888 0.216121 0.933709 0.027 Uiso 1 1 calc R U
H11C H 0.398101 0.222331 0.834646 0.027 Uiso 1 1 calc R U
C16 C 1.1122(3) 0.07751(19) 0.69511(18) 0.0174(5) Uani 1 1 d . .
H16 H 1.168515 0.143356 0.689046 0.021 Uiso 1 1 calc R U
C8 C 0.5081(3) 0.0734(2) 0.86175(16) 0.0153(5) Uani 1 1 d . .
C1 C 0.2220(3) -0.1475(2) 0.92541(17) 0.0166(5) Uani 1 1 d . .
C5 C 0.5164(3) -0.1261(2) 0.84482(17) 0.0147(5) Uani 1 1 d . .
C15 C 1.1685(3) -0.0185(2) 0.65686(17) 0.0156(5) Uani 1 1 d . .
C13 C 0.9414(3) -0.1170(2) 0.71322(17) 0.0168(5) Uani 1 1 d . .
H13 H 0.885186 -0.182926 0.719127 0.020 Uiso 1 1 calc R U
C19 C 1.2704(3) 0.0462(2) 0.51037(19) 0.0252(6) Uani 1 1 d . .
H19A H 1.365586 0.046345 0.477195 0.038 Uiso 1 1 calc R U
H19B H 1.177513 0.010571 0.473529 0.038 Uiso 1 1 calc R U
H19C H 1.240222 0.120540 0.522919 0.038 Uiso 1 1 calc R U
C2 C 0.0717(3) -0.1593(2) 0.96896(18) 0.0198(6) Uani 1 1 d . .
C18 C 1.3145(3) -0.0158(2) 0.60173(18) 0.0170(5) Uani 1 1 d . .
H18A H 1.346825 -0.090462 0.588889 0.020 Uiso 1 1 calc R U
H18B H 1.409587 0.019600 0.638321 0.020 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 0.0033 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C10 N1 C5 117.9(2)
C1 C7 C6 120.3(2)
C1 C7 H7 119.8
C6 C7 H7 119.8
C4 C3 C1 119.0(2)
C4 C3 H3 120.5
C1 C3 H3 120.5
C13 C12 C17 117.8(2)
C13 C12 C10 119.6(2)
C17 C12 C10 122.5(2)
C7 C6 C8 123.1(2)
C7 C6 C5 118.8(2)
C8 C6 C5 118.1(2)
N1 C10 C9 122.3(2)
N1 C10 C12 116.9(2)
C9 C10 C12 120.8(2)
C3 C4 C5 121.5(2)
C3 C4 H4 119.2
C5 C4 H4 119.2
C8 C9 C10 121.3(2)
C8 C9 H9 119.4
C10 C9 H9 119.4
C16 C17 C12 121.1(2)
C16 C17 H17 119.5
C12 C17 H17 119.5
C13 C14 C15 121.4(2)
C13 C14 H14 119.3
C15 C14 H14 119.3
C8 C11 H11A 109.5
C8 C11 H11B 109.5
H11A C11 H11B 109.5
C8 C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
C17 C16 C15 120.9(2)
C17 C16 H16 119.5
C15 C16 H16 119.5
C9 C8 C6 117.3(2)
C9 C8 C11 121.7(2)
C6 C8 C11 120.9(2)
C7 C1 C3 121.1(2)
C7 C1 C2 119.3(2)
C3 C1 C2 119.6(2)
N1 C5 C4 117.7(2)
N1 C5 C6 123.1(2)
C4 C5 C6 119.1(2)
C14 C15 C16 117.9(2)
C14 C15 C18 121.2(2)
C16 C15 C18 120.8(2)
C14 C13 C12 120.8(2)
C14 C13 H13 119.6
C12 C13 H13 119.6
C18 C19 H19A 109.5
C18 C19 H19B 109.5
H19A C19 H19B 109.5
C18 C19 H19C 109.5
H19A C19 H19C 109.5
H19B C19 H19C 109.5
N2 C2 C1 178.7(3)
C15 C18 C19 111.7(2)
C15 C18 H18A 109.3
C19 C18 H18A 109.3
C15 C18 H18B 109.3
C19 C18 H18B 109.3
H18A C18 H18B 107.9
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C10 1.324(3)
N1 C5 1.362(3)
N2 C2 1.145(3)
C7 C1 1.376(3)
C7 C6 1.413(3)
C7 H7 0.9300
C3 C4 1.367(3)
C3 C1 1.421(3)
C3 H3 0.9300
C12 C13 1.398(3)
C12 C17 1.395(3)
C12 C10 1.489(3)
C6 C8 1.420(3)
C6 C5 1.425(3)
C10 C9 1.422(3)
C4 C5 1.413(3)
C4 H4 0.9300
C9 C8 1.369(3)
C9 H9 0.9300
C17 C16 1.388(3)
C17 H17 0.9300
C14 C13 1.384(3)
C14 C15 1.391(3)
C14 H14 0.9300
C11 C8 1.497(3)
C11 H11A 0.9600
C11 H11B 0.9600
C11 H11C 0.9600
C16 C15 1.395(3)
C16 H16 0.9300
C1 C2 1.448(3)
C15 C18 1.511(3)
C13 H13 0.9300
C19 C18 1.526(4)
C19 H19A 0.9600
C19 H19B 0.9600
C19 H19C 0.9600
C18 H18A 0.9700
C18 H18B 0.9700
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
C1 C7 C6 C8 -179.5(2)
C1 C7 C6 C5 0.1(4)
C5 N1 C10 C9 -0.5(4)
C5 N1 C10 C12 -178.6(2)
C13 C12 C10 N1 6.9(3)
C17 C12 C10 N1 -175.2(2)
C13 C12 C10 C9 -171.2(2)
C17 C12 C10 C9 6.8(4)
C1 C3 C4 C5 -0.9(4)
N1 C10 C9 C8 0.3(4)
C12 C10 C9 C8 178.3(2)
C13 C12 C17 C16 1.9(4)
C10 C12 C17 C16 -176.1(2)
C12 C17 C16 C15 -1.3(4)
C10 C9 C8 C6 0.2(4)
C10 C9 C8 C11 -178.6(2)
C7 C6 C8 C9 179.2(2)
C5 C6 C8 C9 -0.4(3)
C7 C6 C8 C11 -2.1(4)
C5 C6 C8 C11 178.3(2)
C6 C7 C1 C3 -0.9(4)
C6 C7 C1 C2 178.6(2)
C4 C3 C1 C7 1.3(4)
C4 C3 C1 C2 -178.2(2)
C10 N1 C5 C4 -179.4(2)
C10 N1 C5 C6 0.3(4)
C3 C4 C5 N1 179.8(2)
C3 C4 C5 C6 0.1(4)
C7 C6 C5 N1 -179.4(2)
C8 C6 C5 N1 0.2(4)
C7 C6 C5 C4 0.3(4)
C8 C6 C5 C4 179.9(2)
C13 C14 C15 C16 0.7(4)
C13 C14 C15 C18 -176.2(2)
C17 C16 C15 C14 0.0(4)
C17 C16 C15 C18 177.0(2)
C15 C14 C13 C12 -0.1(4)
C17 C12 C13 C14 -1.2(4)
C10 C12 C13 C14 176.9(2)
C14 C15 C18 C19 109.2(3)
C16 C15 C18 C19 -67.7(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168350961
