#------------------------------------------------------------------------------
#$Date: 2021-04-05 17:22:44 +0300 (Mon, 05 Apr 2021) $
#$Revision: 263697 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/99/1559980.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_1559980
loop_
_publ_author_name
'Cheng, Yaohang'
'Yu, Shijie'
'He, Yuhang'
'An, Guanghui'
'Li, Guangming'
'Yang, Zhenyu'
_publ_section_title
;
 C4-arylation and domino C4-arylation/3,2-carbonyl migration of indoles by
 tuning Pd catalytic modes: Pd(i)--Pd(ii) catalysis vs. Pd(ii) catalysis
;
_journal_issue                   9
_journal_name_full               'Chemical Science'
_journal_page_first              3216
_journal_page_last               3225
_journal_paper_doi               10.1039/D0SC05409G
_journal_volume                  12
_journal_year                    2021
_chemical_formula_moiety         'C18 H15 N O3'
_chemical_formula_sum            'C18 H15 N O3'
_chemical_formula_weight         293.31
_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   geom
_audit_creation_date             2017-07-24
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2020-09-10 deposited with the CCDC.	2021-01-07 downloaded from the CCDC.
;
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 91.617(5)
_cell_angle_gamma                90.000(5)
_cell_formula_units_Z            4
_cell_length_a                   5.974(5)
_cell_length_b                   16.697(5)
_cell_length_c                   14.741(5)
_cell_measurement_reflns_used    1479
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.5130
_cell_measurement_theta_min      3.4050
_cell_volume                     1469.8(14)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  MoKα
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0232
_diffrn_reflns_av_unetI/netI     0.0350
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            5306
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         3.411
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_correction_T_min  0.978
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_description       block
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         2576
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0837
_refine_ls_R_factor_gt           0.0650
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0633P)²+1.1441P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1609
_refine_ls_wR_factor_ref         0.1724
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1957
_reflns_number_total             2576
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0sc05409g2.cif
_cod_data_source_block           123
_cod_depositor_comments
'Adding full bibliography for 1559980--1559981.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1559980
_shelx_shelxl_version_number     2016/6
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C8(H8), C12(H12), C13(H13), C15(H15), C16(H16), N1(H1)
2.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C18(H18A,H18B,H18C)
;
_olex2_submission_special_instructions 'No special instructions were received'
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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2359(5) 0.14377(18) 0.0445(2) 0.0454(7) Uani 1 1 d . . . . .
C2 C 0.0585(5) 0.1098(2) 0.0895(2) 0.0586(9) Uani 1 1 d . . . . .
H2 H -0.040238 0.076673 0.057272 0.070 Uiso 1 1 calc R . . . .
C3 C 0.0230(6) 0.1235(2) 0.1808(3) 0.0695(10) Uani 1 1 d . . . . .
H3 H -0.100789 0.100866 0.207815 0.083 Uiso 1 1 calc R . . . .
C4 C 0.1678(6) 0.1699(2) 0.2316(2) 0.0673(10) Uani 1 1 d . . . . .
H4 H 0.147705 0.177869 0.293240 0.081 Uiso 1 1 calc R . . . .
C5 C 0.3444(5) 0.20434(19) 0.18789(19) 0.0505(8) Uani 1 1 d . . . . .
C6 C 0.3787(5) 0.19597(17) 0.09395(17) 0.0416(7) Uani 1 1 d . . . . .
C7 C 0.5695(5) 0.24620(17) 0.07480(18) 0.0425(7) Uani 1 1 d . . . . .
C8 C 0.6436(6) 0.27696(19) 0.1572(2) 0.0552(8) Uani 1 1 d . . . . .
H8 H 0.768027 0.309869 0.165606 0.066 Uiso 1 1 calc R . . . .
C9 C 0.6593(5) 0.27070(18) -0.0110(2) 0.0499(8) Uani 1 1 d . . . . .
C10 C 0.8737(6) 0.3166(2) -0.0124(3) 0.0712(10) Uani 1 1 d . . . . .
H10A H 0.896117 0.344242 0.044227 0.107 Uiso 1 1 calc GR . . . .
H10B H 0.866922 0.354808 -0.061115 0.107 Uiso 1 1 calc GR . . . .
H10C H 0.995831 0.280358 -0.021281 0.107 Uiso 1 1 calc GR . . . .
C11 C 0.2825(5) 0.11627(17) -0.0494(2) 0.0440(7) Uani 1 1 d . . . . .
C12 C 0.4889(5) 0.08312(19) -0.0668(2) 0.0510(8) Uani 1 1 d . . . . .
H12 H 0.598614 0.081748 -0.020756 0.061 Uiso 1 1 calc R . . . .
C13 C 0.5359(5) 0.05213(19) -0.1505(2) 0.0507(8) Uani 1 1 d . . . . .
H13 H 0.675502 0.029599 -0.160415 0.061 Uiso 1 1 calc R . . . .
C14 C 0.3759(5) 0.05444(17) -0.21994(19) 0.0436(7) Uani 1 1 d . . . . .
C17 C 0.4233(5) 0.02247(19) -0.3115(2) 0.0521(8) Uani 1 1 d . . . . .
C15 C 0.1674(5) 0.0860(2) -0.2026(2) 0.0537(8) Uani 1 1 d . . . . .
H15 H 0.057077 0.086487 -0.248399 0.064 Uiso 1 1 calc R . . . .
C16 C 0.1207(5) 0.11672(19) -0.1184(2) 0.0509(8) Uani 1 1 d . . . . .
H16 H -0.020228 0.137862 -0.107963 0.061 Uiso 1 1 calc R . . . .
C18 C 0.7078(6) -0.0244(2) -0.4054(2) 0.0697(10) Uani 1 1 d . . . . .
H18A H 0.665580 0.010759 -0.454414 0.104 Uiso 1 1 calc GR . . . .
H18B H 0.636083 -0.075396 -0.414207 0.104 Uiso 1 1 calc GR . . . .
H18C H 0.867341 -0.031499 -0.403750 0.104 Uiso 1 1 calc GR . . . .
N1 N 0.5107(5) 0.25268(17) 0.22326(16) 0.0616(8) Uani 1 1 d . . . . .
H1 H 0.527013 0.265463 0.279572 0.074 Uiso 1 1 calc R . . . .
O1 O 0.5600(5) 0.25585(15) -0.08258(14) 0.0752(8) Uani 1 1 d . . . . .
O2 O 0.6397(4) 0.00969(14) -0.32124(14) 0.0592(6) Uani 1 1 d . . . . .
O3 O 0.2853(4) 0.0108(2) -0.36945(17) 0.0919(10) Uani 1 1 d . . . . .
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
C2 C1 C6 117.7(3) . . ?
C2 C1 C11 118.9(3) . . ?
C6 C1 C11 123.0(3) . . ?
C1 C2 C3 122.5(3) . . ?
C4 C3 C2 120.8(3) . . ?
C3 C4 C5 117.5(3) . . ?
C4 C5 C6 123.5(3) . . ?
N1 C5 C4 128.6(3) . . ?
N1 C5 C6 107.9(3) . . ?
C1 C6 C5 117.8(3) . . ?
C1 C6 C7 136.5(2) . . ?
C5 C6 C7 105.7(3) . . ?
C8 C7 C6 106.1(3) . . ?
C8 C7 C9 123.2(3) . . ?
C9 C7 C6 130.3(3) . . ?
N1 C8 C7 110.3(3) . . ?
C7 C9 C10 119.8(3) . . ?
O1 C9 C7 121.0(3) . . ?
O1 C9 C10 119.2(3) . . ?
C12 C11 C1 119.1(3) . . ?
C12 C11 C16 118.3(3) . . ?
C16 C11 C1 122.4(3) . . ?
C13 C12 C11 121.6(3) . . ?
C12 C13 C14 120.0(3) . . ?
C13 C14 C17 121.2(3) . . ?
C13 C14 C15 118.8(3) . . ?
C15 C14 C17 120.0(3) . . ?
O2 C17 C14 111.6(2) . . ?
O3 C17 C14 124.5(3) . . ?
O3 C17 O2 123.9(3) . . ?
C16 C15 C14 120.9(3) . . ?
C15 C16 C11 120.4(3) . . ?
C8 N1 C5 109.9(2) . . ?
C17 O2 C18 117.4(2) . . ?
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
C1 C2 1.387(4) . ?
C1 C6 1.408(4) . ?
C1 C11 1.492(4) . ?
C2 C3 1.387(5) . ?
C3 C4 1.368(5) . ?
C4 C5 1.377(5) . ?
C5 C6 1.412(4) . ?
C5 N1 1.371(4) . ?
C6 C7 1.449(4) . ?
C7 C8 1.380(4) . ?
C7 C9 1.447(4) . ?
C8 N1 1.336(4) . ?
C9 C10 1.493(5) . ?
C9 O1 1.221(4) . ?
C11 C12 1.382(4) . ?
C11 C16 1.384(4) . ?
C12 C13 1.375(4) . ?
C13 C14 1.381(4) . ?
C14 C17 1.486(4) . ?
C14 C15 1.383(4) . ?
C17 O2 1.322(4) . ?
C17 O3 1.186(4) . ?
C15 C16 1.379(4) . ?
C18 O2 1.434(4) . ?
