#------------------------------------------------------------------------------
#$Date: 2022-03-03 23:14:13 +0200 (Thu, 03 Mar 2022) $
#$Revision: 273265 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/93/4519358.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_4519358
loop_
_publ_author_name
'Murugan, Sivan Perumal'
'Zhong, Hong-Jie'
'Wu, Chih-Yu'
'Pan, Hao-Wei'
'Chen, Chinpiao'
'Lee, Gene-Hsian'
_publ_section_title
;
 Camphorsulfonic Acid-Mediated One-Pot Tandem Consecutive via the Ugi
 Four-Component Reaction for the Synthesis of Functionalized Indole and
 2-Quinolone Derivatives by Switching Solvents.
;
_journal_issue                   7
_journal_name_full               'ACS omega'
_journal_page_first              5713
_journal_page_last               5729
_journal_paper_doi               10.1021/acsomega.1c05460
_journal_volume                  7
_journal_year                    2022
_chemical_formula_sum            'C24 H17 N O'
_chemical_formula_weight         335.38
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 97.6050(11)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.2640(2)
_cell_length_b                   17.8352(5)
_cell_length_c                   15.8767(4)
_cell_measurement_reflns_used    7641
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      29.96
_cell_measurement_theta_min      2.63
_cell_volume                     1758.14(9)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick 2015)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0424
_diffrn_reflns_av_unetI/netI     0.0433
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            15608
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.975
_diffrn_reflns_theta_min         2.625
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.9602
_exptl_absorpt_correction_T_min  0.7328
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.267
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.307
_exptl_crystal_size_mid          0.218
_exptl_crystal_size_min          0.172
_refine_diff_density_max         0.648
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         5096
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0594
_refine_ls_R_factor_gt           0.0493
_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)+(0.0574P)²+0.4861P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1270
_refine_ls_wR_factor_ref         0.1359
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4204
_reflns_number_total             5096
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ao1c05460_si_002.cif
_cod_data_source_block           ic20705
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4519358
_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_min   0.977
_shelx_estimated_absorpt_t_max   0.987
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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_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
O1 O 0.11410(16) 0.57558(6) 0.25815(6) 0.0450(2) Uani 1 1 d . . . . .
N1 N 0.39525(15) 0.52908(5) 0.19743(6) 0.0273(2) Uani 1 1 d . . . . .
C1 C 0.39689(19) 0.58574(6) 0.13515(7) 0.0291(2) Uani 1 1 d . . . . .
C2 C 0.2582(2) 0.64578(7) 0.11410(8) 0.0383(3) Uani 1 1 d . . . . .
H2 H 0.138088 0.654835 0.143453 0.046 Uiso 1 1 calc R U . . .
C3 C 0.3036(3) 0.69193(7) 0.04812(9) 0.0463(3) Uani 1 1 d . . . . .
H3 H 0.212671 0.733647 0.032484 0.056 Uiso 1 1 calc R U . . .
C4 C 0.4774(3) 0.67888(7) 0.00455(9) 0.0460(3) Uani 1 1 d . . . . .
H4 H 0.502598 0.711534 -0.040378 0.055 Uiso 1 1 calc R U . . .
C5 C 0.6148(2) 0.61917(7) 0.02533(8) 0.0386(3) Uani 1 1 d . . . . .
H5 H 0.733830 0.610415 -0.004727 0.046 Uiso 1 1 calc R U . . .
C6 C 0.57416(19) 0.57188(6) 0.09178(7) 0.0288(2) Uani 1 1 d . . . . .
C7 C 0.67983(18) 0.50482(6) 0.12651(7) 0.0277(2) Uani 1 1 d . . . . .
C8 C 0.57015(18) 0.47954(6) 0.18920(7) 0.0260(2) Uani 1 1 d . . . . .
C9 C 0.60295(19) 0.40681(6) 0.23296(7) 0.0285(2) Uani 1 1 d . . . . .
C10 C 0.8016(2) 0.39102(8) 0.28018(8) 0.0386(3) Uani 1 1 d . . . . .
H10 H 0.908167 0.429127 0.289332 0.046 Uiso 1 1 calc R U . . .
C11 C 0.8448(2) 0.32008(9) 0.31386(9) 0.0473(3) Uani 1 1 d . . . . .
H11 H 0.981018 0.309551 0.345518 0.057 Uiso 1 1 calc R U . . .
C12 C 0.6890(3) 0.26446(8) 0.30132(9) 0.0479(4) Uani 1 1 d . . . . .
H12 H 0.718553 0.215789 0.324246 0.057 Uiso 1 1 calc R U . . .
C13 C 0.4900(3) 0.28001(8) 0.25526(9) 0.0444(3) Uani 1 1 d . . . . .
H13 H 0.383087 0.241971 0.247040 0.053 Uiso 1 1 calc R U . . .
C14 C 0.4464(2) 0.35076(7) 0.22117(8) 0.0351(3) Uani 1 1 d . . . . .
H14 H 0.309745 0.361122 0.189751 0.042 Uiso 1 1 calc R U . . .
C15 C 0.8642(2) 0.46782(7) 0.09247(8) 0.0351(3) Uani 1 1 d . . . . .
H15A H 0.894383 0.419492 0.120932 0.053 Uiso 1 1 calc R U . . .
H15B H 0.991840 0.499971 0.102905 0.053 Uiso 1 1 calc R U . . .
H15C H 0.827458 0.459710 0.031217 0.053 Uiso 1 1 calc R U . . .
C16 C 0.26556(19) 0.53256(7) 0.26195(7) 0.0313(2) Uani 1 1 d . . . . .
C17 C 0.3185(2) 0.48411(7) 0.33470(7) 0.0344(3) Uani 1 1 d . . . . .
C18 C 0.3380(2) 0.45067(8) 0.40059(7) 0.0367(3) Uani 1 1 d . . . . .
C19 C 0.3715(2) 0.40924(7) 0.47845(7) 0.0343(3) Uani 1 1 d . . . . .
C20 C 0.2170(2) 0.41014(8) 0.53446(9) 0.0434(3) Uani 1 1 d . . . . .
H20 H 0.087028 0.437524 0.520534 0.052 Uiso 1 1 calc R U . . .
C21 C 0.2543(3) 0.37081(9) 0.61065(9) 0.0483(4) Uani 1 1 d . . . . .
H21 H 0.149872 0.371508 0.648943 0.058 Uiso 1 1 calc R U . . .
C22 C 0.4418(3) 0.33097(9) 0.63059(9) 0.0465(3) Uani 1 1 d . . . . .
H22 H 0.466246 0.303914 0.682513 0.056 Uiso 1 1 calc R U . . .
C23 C 0.5951(3) 0.33007(9) 0.57542(9) 0.0477(3) Uani 1 1 d . . . . .
H23 H 0.724662 0.302575 0.589775 0.057 Uiso 1 1 calc R U . . .
C24 C 0.5610(2) 0.36884(8) 0.49970(8) 0.0415(3) Uani 1 1 d . . . . .
H24 H 0.666856 0.367978 0.462041 0.050 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'
O O 0.0106 0.0060 '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
C16 N1 C1 122.83(10) . . ?
C16 N1 C8 128.72(10) . . ?
C1 N1 C8 107.55(9) . . ?
C2 C1 C6 121.80(11) . . ?
C2 C1 N1 130.96(11) . . ?
C6 C1 N1 107.24(10) . . ?
C3 C2 C1 116.94(13) . . ?
C4 C3 C2 121.97(13) . . ?
C5 C4 C3 121.08(12) . . ?
C4 C5 C6 118.35(13) . . ?
C5 C6 C1 119.86(12) . . ?
C5 C6 C7 131.94(12) . . ?
C1 C6 C7 108.16(9) . . ?
C8 C7 C6 107.73(10) . . ?
C8 C7 C15 127.52(11) . . ?
C6 C7 C15 124.53(10) . . ?
C7 C8 N1 109.29(10) . . ?
C7 C8 C9 125.81(10) . . ?
N1 C8 C9 124.26(9) . . ?
C10 C9 C14 119.28(11) . . ?
C10 C9 C8 119.37(11) . . ?
C14 C9 C8 121.05(10) . . ?
C11 C10 C9 120.42(13) . . ?
C10 C11 C12 119.98(13) . . ?
C13 C12 C11 119.92(12) . . ?
C14 C13 C12 120.32(13) . . ?
C13 C14 C9 120.07(13) . . ?
O1 C16 N1 121.33(11) . . ?
O1 C16 C17 120.80(11) . . ?
N1 C16 C17 117.87(11) . . ?
C18 C17 C16 169.37(14) . . ?
C17 C18 C19 177.11(15) . . ?
C24 C19 C20 119.46(12) . . ?
C24 C19 C18 119.96(12) . . ?
C20 C19 C18 120.57(13) . . ?
C21 C20 C19 119.78(14) . . ?
C22 C21 C20 120.09(13) . . ?
C21 C22 C23 120.29(13) . . ?
C24 C23 C22 120.40(14) . . ?
C23 C24 C19 119.98(13) . . ?
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
O1 C16 1.2155(15) . ?
N1 C16 1.3904(14) . ?
N1 C1 1.4148(14) . ?
N1 C8 1.4269(14) . ?
C1 C2 1.3913(17) . ?
C1 C6 1.4039(17) . ?
C2 C3 1.3909(19) . ?
C3 C4 1.385(2) . ?
C4 C5 1.381(2) . ?
C5 C6 1.4001(16) . ?
C6 C7 1.4408(16) . ?
C7 C8 1.3591(15) . ?
C7 C15 1.4921(16) . ?
C8 C9 1.4730(15) . ?
C9 C10 1.3941(17) . ?
C9 C14 1.3956(16) . ?
C10 C11 1.3862(19) . ?
C11 C12 1.387(2) . ?
C12 C13 1.387(2) . ?
C13 C14 1.3860(18) . ?
C16 C17 1.4454(17) . ?
C17 C18 1.1963(18) . ?
C18 C19 1.4317(17) . ?
C19 C24 1.391(2) . ?
C19 C20 1.3983(18) . ?
C20 C21 1.391(2) . ?
C21 C22 1.373(2) . ?
C22 C23 1.383(2) . ?
C23 C24 1.379(2) . ?
