#------------------------------------------------------------------------------
#$Date: 2020-03-05 02:28:23 +0200 (Thu, 05 Mar 2020) $
#$Revision: 249028 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/73/7157303.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_7157303
loop_
_publ_author_name
'Ramanathan, Mani'
'Wan, Jing'
'Liu, Yi-Hung'
'Peng, Shie-Ming'
'Liu, Shiuh-Tzung'
_publ_section_title
;
 Synthesis of 2-arylamino-3-cyanoquinolines via a cascade reaction through
 a nitrilium intermediate.
;
_journal_issue                   5
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              975
_journal_page_last               982
_journal_paper_doi               10.1039/c9ob02427a
_journal_volume                  18
_journal_year                    2020
_chemical_formula_sum            'C25 H21 N3'
_chemical_formula_weight         363.45
_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   mixed
_audit_creation_method           SHELXL-2017/1
_audit_update_record
;
2019-09-20 deposited with the CCDC.	2020-01-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.886(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.6501(4)
_cell_length_b                   10.8130(3)
_cell_length_c                   16.4196(5)
_cell_measurement_reflns_used    4543
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      29.0090
_cell_measurement_theta_min      3.8210
_cell_volume                     1979.24(11)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 10.2496
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0284
_diffrn_reflns_av_unetI/netI     0.0372
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10903
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_min         3.154
_diffrn_source                   'fine-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89892
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_crystal_density_diffrn    1.220
_exptl_crystal_description       plate
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.492
_refine_diff_density_min         -0.449
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       0.009(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         4442
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.0825
_refine_ls_R_factor_gt           0.0599
_refine_ls_shift/su_max          0.018
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0944P)²+1.4059P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1657
_refine_ls_wR_factor_ref         0.1887
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3276
_reflns_number_total             4442
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9ob02427a2.cif
_cod_data_source_block           ic19402
_cod_depositor_comments          'Adding full bibliography for 7157303.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7157303
_shelx_shelxl_version_number     2017/1
_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 0.79410(15) 0.41789(15) 0.35123(10) 0.0259(4) Uani 1 1 d . .
N2 N 0.66748(16) 0.54616(16) 0.39735(11) 0.0281(4) Uani 1 1 d . .
H2 H 0.615(2) 0.553(2) 0.4218(17) 0.042 Uiso 1 1 d . U
N3 N 0.51839(18) 0.36492(17) 0.51346(13) 0.0385(5) Uani 1 1 d . .
C1 C 0.85407(17) 0.30797(18) 0.35683(12) 0.0253(4) Uani 1 1 d . .
C2 C 0.9407(2) 0.2971(2) 0.31214(14) 0.0329(5) Uani 1 1 d . .
H2A H 0.950075 0.361933 0.275529 0.039 Uiso 1 1 calc R U
C3 C 1.0114(2) 0.1934(2) 0.32138(15) 0.0367(5) Uani 1 1 d . .
H3A H 1.070342 0.187740 0.291948 0.044 Uiso 1 1 calc R U
C4 C 0.9972(2) 0.0958(2) 0.37386(14) 0.0347(5) Uani 1 1 d . .
H4A H 1.048474 0.025735 0.381178 0.042 Uiso 1 1 calc R U
C5 C 0.91045(18) 0.10056(19) 0.41451(13) 0.0289(4) Uani 1 1 d . .
H5A H 0.899616 0.032551 0.448157 0.035 Uiso 1 1 calc R U
C6 C 0.83632(17) 0.20662(17) 0.40676(12) 0.0244(4) Uani 1 1 d . .
C7 C 0.74710(17) 0.21986(17) 0.45042(11) 0.0234(4) Uani 1 1 d . .
C8 C 0.68991(17) 0.33252(18) 0.44564(12) 0.0240(4) Uani 1 1 d . .
C9 C 0.71903(17) 0.43325(17) 0.39666(11) 0.0236(4) Uani 1 1 d . .
C10 C 0.71628(18) 0.11544(18) 0.49914(12) 0.0260(4) Uani 1 1 d . .
C11 C 0.6765(2) 0.0039(2) 0.45819(14) 0.0332(5) Uani 1 1 d . .
H11A H 0.670304 -0.005566 0.399550 0.040 Uiso 1 1 calc R U
C12 C 0.6459(2) -0.0932(2) 0.50266(17) 0.0437(6) Uani 1 1 d . .
H12A H 0.617874 -0.168771 0.474309 0.052 Uiso 1 1 calc R U
C13 C 0.6559(2) -0.0806(2) 0.58801(17) 0.0472(6) Uani 1 1 d . .
H13A H 0.634702 -0.147540 0.618256 0.057 Uiso 1 1 calc R U
C14 C 0.6969(2) 0.0291(2) 0.62976(15) 0.0435(6) Uani 1 1 d . .
H14A H 0.704461 0.037136 0.688712 0.052 Uiso 1 1 calc R U
C15 C 0.7268(2) 0.1273(2) 0.58543(13) 0.0328(5) Uani 1 1 d . .
H15A H 0.754471 0.202809 0.614024 0.039 Uiso 1 1 calc R U
C16 C 0.59542(19) 0.34922(18) 0.48471(13) 0.0274(4) Uani 1 1 d . .
C17 C 0.69137(18) 0.65107(17) 0.35144(12) 0.0251(4) Uani 1 1 d . .
C18 C 0.80666(18) 0.70086(18) 0.37039(13) 0.0288(5) Uani 1 1 d . .
C19 C 0.82630(19) 0.79867(18) 0.32103(13) 0.0310(5) Uani 1 1 d . .
H19A H 0.905120 0.831234 0.332388 0.037 Uiso 1 1 calc R U
C20 C 0.7352(2) 0.85055(18) 0.25582(13) 0.0303(5) Uani 1 1 d . .
C21 C 0.62017(19) 0.80456(18) 0.24276(13) 0.0293(5) Uani 1 1 d . .
H21A H 0.555665 0.842468 0.201074 0.035 Uiso 1 1 calc R U
C22 C 0.59601(18) 0.70449(18) 0.28880(12) 0.0269(4) Uani 1 1 d . .
C23 C 0.9092(2) 0.6530(2) 0.44282(16) 0.0445(6) Uani 1 1 d . .
H23A H 0.880827 0.584571 0.471070 0.067 Uiso 1 1 calc R U
H23B H 0.973715 0.623686 0.420509 0.067 Uiso 1 1 calc R U
H23C H 0.939408 0.719683 0.483868 0.067 Uiso 1 1 calc R U
C24 C 0.7598(2) 0.9526(2) 0.20006(17) 0.0445(6) Uani 1 1 d . .
H24A H 0.845454 0.973128 0.218477 0.067 Uiso 1 1 calc R U
H24B H 0.737106 0.924726 0.140720 0.067 Uiso 1 1 calc R U
H24C H 0.712902 1.025998 0.204880 0.067 Uiso 1 1 calc R U
C25 C 0.4701(2) 0.6553(2) 0.27013(15) 0.0398(5) Uani 1 1 d . .
H25A H 0.469112 0.585498 0.307986 0.060 Uiso 1 1 calc R U
H25B H 0.417149 0.720782 0.279452 0.060 Uiso 1 1 calc R U
H25C H 0.442147 0.627609 0.210804 0.060 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
C9 N1 C1 118.85(16)
C9 N2 C17 123.47(17)
N1 C1 C2 117.68(17)
N1 C1 C6 123.53(17)
C2 C1 C6 118.76(18)
C3 C2 C1 120.36(19)
C2 C3 C4 120.6(2)
C5 C4 C3 120.51(19)
C4 C5 C6 120.33(19)
C5 C6 C1 119.26(18)
C5 C6 C7 123.20(17)
C1 C6 C7 117.46(17)
C8 C7 C6 117.95(17)
C8 C7 C10 120.87(17)
C6 C7 C10 121.18(17)
C7 C8 C16 120.34(17)
C7 C8 C9 120.49(17)
C16 C8 C9 119.06(17)
N1 C9 N2 119.05(17)
N1 C9 C8 121.38(17)
N2 C9 C8 119.57(17)
C15 C10 C11 119.32(18)
C15 C10 C7 120.92(18)
C11 C10 C7 119.77(17)
C12 C11 C10 120.2(2)
C13 C12 C11 120.2(2)
C12 C13 C14 120.2(2)
C13 C14 C15 119.9(2)
C14 C15 C10 120.1(2)
N3 C16 C8 177.7(2)
C18 C17 C22 120.75(18)
C18 C17 N2 120.62(17)
C22 C17 N2 118.61(18)
C19 C18 C17 118.28(18)
C19 C18 C23 119.53(19)
C17 C18 C23 122.19(19)
C20 C19 C18 122.57(19)
C21 C20 C19 117.54(19)
C21 C20 C24 120.8(2)
C19 C20 C24 121.6(2)
C20 C21 C22 122.18(19)
C21 C22 C17 118.43(19)
C21 C22 C25 120.11(18)
C17 C22 C25 121.46(18)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C9 1.315(2)
N1 C1 1.368(3)
N2 C9 1.362(3)
N2 C17 1.433(3)
N3 C16 1.142(3)
C1 C2 1.415(3)
C1 C6 1.419(3)
C2 C3 1.373(3)
C3 C4 1.402(3)
C4 C5 1.365(3)
C5 C6 1.419(3)
C6 C7 1.431(3)
C7 C8 1.380(3)
C7 C10 1.487(3)
C8 C16 1.438(3)
C8 C9 1.451(3)
C10 C15 1.392(3)
C10 C11 1.393(3)
C11 C12 1.383(3)
C12 C13 1.379(4)
C13 C14 1.384(4)
C14 C15 1.389(3)
C17 C18 1.396(3)
C17 C22 1.401(3)
C18 C19 1.391(3)
C18 C23 1.511(3)
C19 C20 1.388(3)
C20 C21 1.387(3)
C20 C24 1.514(3)
C21 C22 1.395(3)
C22 C25 1.506(3)
