#------------------------------------------------------------------------------
#$Date: 2020-09-06 13:18:04 +0300 (Sun, 06 Sep 2020) $
#$Revision: 256164 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/76/7157631.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_7157631
loop_
_publ_author_name
'Cheng, Li-Ting'
'Luo, Sheng-Qi'
'Hong, Bor-Cherng'
'Chen, Chia-Ling'
'Li, Wen-Shan'
'Lee, Gene-Hsiang'
_publ_section_title
;
 Oxidative trimerization of indoles via water-assisted visible-light
 photoredox catalysis and the study of their anti-cancer activities.
;
_journal_issue                   32
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              6247
_journal_page_last               6252
_journal_paper_doi               10.1039/d0ob01298j
_journal_volume                  18
_journal_year                    2020
_chemical_formula_sum            'C24 H17.19 N3 O1.1'
_chemical_formula_weight         365.12
_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   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2020-05-25 deposited with the CCDC.	2020-07-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.7088(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.5627(3)
_cell_length_b                   8.8564(3)
_cell_length_c                   19.8868(7)
_cell_measurement_reflns_used    9796
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      75.06
_cell_measurement_theta_min      4.48
_cell_volume                     1838.91(10)
_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-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0169
_diffrn_reflns_av_unetI/netI     0.0159
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            12050
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.982
_diffrn_reflns_theta_min         4.484
_exptl_absorpt_coefficient_mu    0.657
_exptl_absorpt_correction_T_max  0.7539
_exptl_absorpt_correction_T_min  0.6813
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_crystal_colour            light-brown
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_description       plate
_exptl_crystal_F_000             764
_exptl_crystal_size_max          0.232
_exptl_crystal_size_mid          0.162
_exptl_crystal_size_min          0.048
_refine_diff_density_max         0.251
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         3770
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.0399
_refine_ls_R_factor_gt           0.0365
_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)+(0.0454P)²+0.6822P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0919
_refine_ls_wR_factor_ref         0.0964
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3459
_reflns_number_total             3770
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ob01298j2.cif
_cod_data_source_block           ic19115
_cod_depositor_comments
'Adding full bibliography for 7157631--7157635.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_original_formula_sum        'C24 H17.19 N3 O1.10'
_cod_database_code               7157631
_shelx_shelxl_version_number     2014/7
_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   0.862
_shelx_estimated_absorpt_t_max   0.969
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 -0.03541(7) 0.56666(9) 0.15854(4) 0.02656(18) Uani 1 1 d . . . . .
N1 N -0.04608(10) 0.95604(12) 0.11869(5) 0.0300(2) Uani 1 1 d . . . . .
H1 H -0.0237(17) 1.050(2) 0.1248(9) 0.052(5) Uiso 1 1 d . . . . .
N2 N 0.31920(10) 0.89896(13) 0.26218(5) 0.0343(2) Uani 1 1 d . . . . .
H2 H 0.3757(18) 0.946(2) 0.2930(9) 0.053(5) Uiso 1 1 d . . . . .
N3 N -0.24512(10) 0.95183(13) 0.28314(6) 0.0366(2) Uani 1 1 d . . . . .
H3 H -0.3133(18) 1.004(2) 0.2922(9) 0.055(5) Uiso 1 1 d . . . . .
C1 C -0.00968(10) 0.84217(12) 0.17204(5) 0.0240(2) Uani 1 1 d . . . . .
C2 C -0.05118(10) 0.69331(12) 0.13337(5) 0.0234(2) Uani 1 1 d . . . . .
C3 C -0.10944(11) 0.73445(14) 0.06549(6) 0.0303(3) Uani 1 1 d . . . . .
C4 C -0.15999(16) 0.64515(17) 0.00979(7) 0.0468(4) Uani 1 1 d . . . . .
H4 H -0.1632 0.5384 0.0138 0.056 Uiso 1 1 calc R U . . .
C5 C -0.20500(18) 0.7152(2) -0.05089(8) 0.0589(5) Uani 1 1 d . . . . .
H5 H -0.2395 0.6568 -0.0894 0.071 Uiso 1 1 calc R U . . .
C6 C -0.19985(14) 0.87319(19) -0.05584(7) 0.0485(4) Uani 1 1 d . . . . .
H6 H -0.2323 0.9196 -0.0980 0.058 Uiso 1 1 calc R U . . .
C7 C -0.14971(11) 0.96340(16) -0.00201(6) 0.0357(3) Uani 1 1 d . . . . .
H7 H -0.1471 1.0701 -0.0065 0.043 Uiso 1 1 calc R U . . .
C8 C -0.10260(10) 0.89212(14) 0.05976(6) 0.0282(2) Uani 1 1 d . . . . .
C9 C 0.18931(11) 0.91630(14) 0.25490(6) 0.0302(2) Uani 1 1 d . . . . .
H9 H 0.1451 0.9709 0.2853 0.036 Uiso 1 1 calc R U . . .
C10 C 0.13228(10) 0.84375(12) 0.19762(5) 0.0242(2) Uani 1 1 d . . . . .
C11 C 0.23386(10) 0.77851(12) 0.16614(5) 0.0237(2) Uani 1 1 d . . . . .
C12 C 0.24067(11) 0.69429(13) 0.10702(6) 0.0275(2) Uani 1 1 d . . . . .
H12 H 0.1648 0.6678 0.0774 0.033 Uiso 1 1 calc R U . . .
C13 C 0.35930(12) 0.65023(14) 0.09239(6) 0.0334(3) Uani 1 1 d . . . . .
H13 H 0.3642 0.5942 0.0521 0.040 Uiso 1 1 calc R U . . .
C14 C 0.47245(12) 0.68676(15) 0.13591(7) 0.0363(3) Uani 1 1 d . . . . .
H14 H 0.5525 0.6541 0.1249 0.044 Uiso 1 1 calc R U . . .
C15 C 0.46907(12) 0.76920(15) 0.19427(7) 0.0353(3) Uani 1 1 d . . . . .
H15 H 0.5455 0.7938 0.2239 0.042 Uiso 1 1 calc R U . . .
C16 C 0.34991(11) 0.81536(13) 0.20856(6) 0.0285(2) Uani 1 1 d . . . . .
C17 C -0.19112(11) 0.96207(14) 0.22508(6) 0.0320(3) Uani 1 1 d . . . . .
H17 H -0.2188 1.0283 0.1882 0.038 Uiso 1 1 calc R U . . .
C18 C -0.09133(10) 0.86286(13) 0.22791(6) 0.0256(2) Uani 1 1 d . . . . .
C19 C -0.08362(11) 0.78394(13) 0.29171(6) 0.0268(2) Uani 1 1 d . . . . .
C20 C -0.00512(12) 0.67001(14) 0.32449(6) 0.0323(3) Uani 1 1 d . . . . .
H20 H 0.0617 0.6274 0.3036 0.039 Uiso 1 1 calc R U . . .
C21 C -0.02689(14) 0.62076(17) 0.38788(7) 0.0420(3) Uani 1 1 d . . . . .
H21 H 0.0252 0.5427 0.4102 0.050 Uiso 1 1 calc R U . . .
C22 C -0.12394(16) 0.68347(18) 0.41979(7) 0.0469(4) Uani 1 1 d . . . . .
H22 H -0.1355 0.6483 0.4636 0.056 Uiso 1 1 calc R U . . .
C23 C -0.20285(14) 0.79484(17) 0.38901(7) 0.0430(3) Uani 1 1 d . . . . .
H23 H -0.2691 0.8368 0.4106 0.052 Uiso 1 1 calc R U . . .
C24 C -0.18203(12) 0.84414(14) 0.32489(6) 0.0327(3) Uani 1 1 d . . . . .
O2 O -0.0240(14) 1.2884(13) 0.0876(8) 0.067(5) Uani 0.098(4) 1 d . . P . .
H2A H -0.0252 1.3794 0.1011 0.101 Uiso 0.098(4) 1 d R U P . .
H2B H 0.0531 1.2597 0.0988 0.101 Uiso 0.098(4) 1 d R U P . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C8 N1 C1 111.70(9) . . ?
C9 N2 C16 109.20(10) . . ?
C17 N3 C24 109.36(10) . . ?
N1 C1 C10 111.99(9) . . ?
N1 C1 C18 109.25(9) . . ?
C10 C1 C18 113.46(9) . . ?
N1 C1 C2 101.59(8) . . ?
C10 C1 C2 111.46(9) . . ?
C18 C1 C2 108.39(9) . . ?
O1 C2 C3 128.58(10) . . ?
O1 C2 C1 124.15(9) . . ?
C3 C2 C1 107.27(9) . . ?
C4 C3 C8 121.07(11) . . ?
C4 C3 C2 130.95(12) . . ?
C8 C3 C2 107.89(10) . . ?
C5 C4 C3 118.62(14) . . ?
C4 C5 C6 119.92(14) . . ?
C7 C6 C5 122.58(12) . . ?
C6 C7 C8 117.61(12) . . ?
N1 C8 C7 128.31(12) . . ?
N1 C8 C3 111.51(10) . . ?
C7 C8 C3 120.17(11) . . ?
C10 C9 N2 110.15(10) . . ?
C9 C10 C11 106.70(10) . . ?
C9 C10 C1 125.16(10) . . ?
C11 C10 C1 128.07(10) . . ?
C12 C11 C16 118.15(10) . . ?
C12 C11 C10 135.43(10) . . ?
C16 C11 C10 106.42(10) . . ?
C13 C12 C11 119.25(11) . . ?
C12 C13 C14 121.25(11) . . ?
C15 C14 C13 120.94(11) . . ?
C14 C15 C16 117.86(11) . . ?
N2 C16 C15 129.94(11) . . ?
N2 C16 C11 107.51(10) . . ?
C15 C16 C11 122.54(11) . . ?
N3 C17 C18 109.92(11) . . ?
C17 C18 C19 106.78(10) . . ?
C17 C18 C1 124.60(11) . . ?
C19 C18 C1 128.61(10) . . ?
C20 C19 C24 118.55(11) . . ?
C20 C19 C18 135.18(11) . . ?
C24 C19 C18 106.27(10) . . ?
C21 C20 C19 118.79(12) . . ?
C20 C21 C22 121.43(14) . . ?
C23 C22 C21 121.29(13) . . ?
C22 C23 C24 117.55(13) . . ?
N3 C24 C23 129.94(12) . . ?
N3 C24 C19 107.67(11) . . ?
C23 C24 C19 122.39(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 C2 1.2292(13) . ?
N1 C8 1.3558(15) . ?
N1 C1 1.4722(14) . ?
N2 C9 1.3663(16) . ?
N2 C16 1.3768(16) . ?
N3 C17 1.3660(17) . ?
N3 C24 1.3695(18) . ?
C1 C10 1.5088(15) . ?
C1 C18 1.5172(15) . ?
C1 C2 1.5555(15) . ?
C2 C3 1.4431(15) . ?
C3 C4 1.3994(18) . ?
C3 C8 1.4038(17) . ?
C4 C5 1.376(2) . ?
C5 C6 1.404(2) . ?
C6 C7 1.376(2) . ?
C7 C8 1.4037(16) . ?
C9 C10 1.3658(16) . ?
C10 C11 1.4423(15) . ?
C11 C12 1.4034(16) . ?
C11 C16 1.4169(15) . ?
C12 C13 1.3847(17) . ?
C13 C14 1.4031(19) . ?
C14 C15 1.3761(19) . ?
C15 C16 1.3929(17) . ?
C17 C18 1.3668(16) . ?
C18 C19 1.4400(16) . ?
C19 C20 1.4025(17) . ?
C19 C24 1.4170(16) . ?
C20 C21 1.3857(18) . ?
C21 C22 1.400(2) . ?
C22 C23 1.374(2) . ?
C23 C24 1.3963(18) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O2 0.87(2) 2.24(2) 3.024(12) 150.6(16) .
N2 H2 O1 0.890(19) 2.105(19) 2.9693(13) 163.5(16) 2
N3 H3 O1 0.89(2) 2.07(2) 2.9271(13) 159.2(16) 2_455
