#------------------------------------------------------------------------------
#$Date: 2022-06-22 09:23:47 +0300 (Wed, 22 Jun 2022) $
#$Revision: 276143 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/99/1559981.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_1559981
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         586.62
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2017-08-06
_audit_creation_method
;
Olex2 1.2
(compiled 2017.07.20 svn.r3457 for OlexSys, GUI svn.r5370)
;
_audit_update_record
;
2020-09-10 deposited with the CCDC.	2021-01-07 downloaded from the CCDC.
;
_cell_angle_alpha                96.901(8)
_cell_angle_beta                 107.557(9)
_cell_angle_gamma                92.751(8)
_cell_formula_units_Z            2
_cell_length_a                   8.1516(8)
_cell_length_b                   8.1871(8)
_cell_length_c                   11.8093(11)
_cell_measurement_reflns_used    1512
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.6755
_cell_measurement_theta_min      3.3060
_cell_volume                     743.01(13)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.1954
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   46.00   80.00   1.0000    5.3100
omega____ theta____ kappa____ phi______ frames
    -       25.5830  178.0000 -150.0000 34

#__ type_ start__ end____ width___ exp.time_
  2 omega  -24.00   55.00   1.0000    5.3100
omega____ theta____ kappa____ phi______ frames
    -       25.5830  -99.0000   60.0000 79

#__ type_ start__ end____ width___ exp.time_
  3 omega   75.00  102.00   1.0000    5.3100
omega____ theta____ kappa____ phi______ frames
    -       25.5830   38.0000  120.0000 27

#__ type_ start__ end____ width___ exp.time_
  4 omega -100.00   -8.00   1.0000    5.3100
omega____ theta____ kappa____ phi______ frames
    -      -26.8330  -57.0000 -180.0000 92

#__ type_ start__ end____ width___ exp.time_
  5 omega    9.00   48.00   1.0000    5.3100
omega____ theta____ kappa____ phi______ frames
    -      -26.8330   77.0000   60.0000 39

#__ type_ start__ end____ width___ exp.time_
  6 omega  -25.00   20.00   1.0000    5.3100
omega____ theta____ kappa____ phi______ frames
    -      -26.8330  -99.0000  120.0000 45

#__ type_ start__ end____ width___ exp.time_
  7 omega  -56.00   37.00   1.0000    5.3100
omega____ theta____ kappa____ phi______ frames
    -      -26.8330   57.0000  -30.0000 93

#__ type_ start__ end____ width___ exp.time_
  8 omega  -12.00   13.00   1.0000    5.3100
omega____ theta____ kappa____ phi______ frames
    -      -26.8330  -99.0000  -60.0000 25
;
_diffrn_measurement_device_type  MoKα
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0172126000
_diffrn_orient_matrix_UB_12      -0.0530386000
_diffrn_orient_matrix_UB_13      0.0446971000
_diffrn_orient_matrix_UB_21      -0.0143982000
_diffrn_orient_matrix_UB_22      -0.0693795000
_diffrn_orient_matrix_UB_23      -0.0450836000
_diffrn_orient_matrix_UB_31      0.0888375000
_diffrn_orient_matrix_UB_32      0.0070745000
_diffrn_orient_matrix_UB_33      0.0043806000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0150
_diffrn_reflns_av_unetI/netI     0.0276
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4629
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         3.313
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_correction_T_min  0.983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_description       block
_exptl_crystal_F_000             308
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.702
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         2615
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.702
_refine_ls_R_factor_all          0.0600
_refine_ls_R_factor_gt           0.0453
_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)+(0.1310P)²+0.4060P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1279
_refine_ls_wR_factor_ref         0.1532
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2012
_reflns_number_total             2615
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0sc05409g2.cif
_cod_data_source_block           20170803agh
_cod_depositor_comments
;
Adding full bibliography for 1559980--1559981.cif.

2022-06-21
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C12 H10 N0.67 O2'
_cod_original_formula_weight         195.54
_cod_original_formula_moiety         '0.67(C18 H15 N O3)'
_cod_original_formula_units_Z            3
_cod_original_cell_volume        743.02(13)
_cod_database_code               1559981
_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.
;
_shelx_estimated_absorpt_t_max   0.989
_shelx_estimated_absorpt_t_min   0.981
_reflns_odcompleteness_completeness 99.80
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.50
_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:
 N1(H1), C5(H5), C6(H6), C8(H8), C13(H13), C16(H16), C18(H18), C19(H19),
 C20(H20)
2.b Idealised Me refined as rotating group:
 C0AA(H0AA,H0AB,H0AC), C1AA(H1AA,H1AB,H1AC)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
N1 N 0.20093(19) 0.98342(19) 0.92625(14) 0.0457(4) Uani 1 1 d . . . . .
H1 H 0.128764 1.035468 0.953793 0.055 Uiso 1 1 calc R . . . .
C2 C 0.6013(2) 0.8201(2) 0.72202(16) 0.0428(4) Uani 1 1 d . . . . .
C3 C 0.8016(2) 0.5797(2) 0.65796(16) 0.0441(5) Uani 1 1 d . . . . .
C4 C 0.4936(2) 0.9479(2) 0.75387(17) 0.0450(5) Uani 1 1 d . . . . .
C5 C 0.7746(2) 0.8588(3) 0.73444(18) 0.0509(5) Uani 1 1 d . . . . .
H5 H 0.824129 0.966300 0.763645 0.061 Uiso 1 1 calc R . . . .
C6 C 0.5298(3) 0.6591(2) 0.67665(18) 0.0477(5) Uani 1 1 d . . . . .
H6 H 0.414479 0.630782 0.668230 0.057 Uiso 1 1 calc R . . . .
C7 C 0.2841(2) 1.0404(2) 0.85316(17) 0.0436(4) Uani 1 1 d . . . . .
C8 C 0.6284(3) 0.5410(2) 0.64403(18) 0.0481(5) Uani 1 1 d . . . . .
H8 H 0.578308 0.434293 0.612355 0.058 Uiso 1 1 calc R . . . .
O9 O 0.8197(2) 0.31036(19) 0.57475(15) 0.0664(5) Uani 1 1 d . . . . .
O10 O 0.05975(19) 0.79026(18) 1.05871(14) 0.0612(4) Uani 1 1 d . . . . .
C11 C 0.1740(2) 0.7363(2) 1.02097(17) 0.0474(5) Uani 1 1 d . . . . .
C12 C 0.3908(2) 0.9186(2) 0.82825(17) 0.0423(4) Uani 1 1 d . . . . .
C13 C 0.8736(2) 0.7396(3) 0.70391(18) 0.0515(5) Uani 1 1 d . . . . .
H13 H 0.989780 0.766886 0.714264 0.062 Uiso 1 1 calc R . . . .
C14 C 0.2502(2) 0.8293(2) 0.94938(16) 0.0427(4) Uani 1 1 d . . . . .
C15 C 0.9117(3) 0.4546(3) 0.62526(18) 0.0521(5) Uani 1 1 d . . . . .
C16 C 0.3679(2) 0.7874(2) 0.89129(16) 0.0430(4) Uani 1 1 d . . . . .
H16 H 0.422691 0.690264 0.893024 0.052 Uiso 1 1 calc R . . . .
O17 O 1.0640(2) 0.4781(2) 0.64195(17) 0.0762(5) Uani 1 1 d . . . . .
C18 C 0.2741(3) 1.1877(2) 0.8049(2) 0.0548(5) Uani 1 1 d . . . . .
H18 H 0.201164 1.265488 0.820155 0.066 Uiso 1 1 calc R . . . .
C19 C 0.4845(3) 1.0962(3) 0.7094(2) 0.0576(6) Uani 1 1 d . . . . .
H19 H 0.552375 1.119244 0.661593 0.069 Uiso 1 1 calc R . . . .
C20 C 0.3752(3) 1.2137(3) 0.7342(2) 0.0618(6) Uani 1 1 d . . . . .
H20 H 0.371826 1.311884 0.701586 0.074 Uiso 1 1 calc R . . . .
C0AA C 0.2356(3) 0.5704(3) 1.0454(2) 0.0613(6) Uani 1 1 d . . . . .
H0AA H 0.203301 0.538456 1.111927 0.092 Uiso 1 1 calc GR . . . .
H0AB H 0.358976 0.576400 1.064316 0.092 Uiso 1 1 calc GR . . . .
H0AC H 0.183777 0.490177 0.975665 0.092 Uiso 1 1 calc GR . . . .
C1AA C 0.9088(4) 0.1808(3) 0.5328(3) 0.0776(8) Uani 1 1 d . . . . .
H1AA H 0.994260 0.227604 0.502262 0.116 Uiso 1 1 calc GR . . . .
H1AB H 0.827527 0.105508 0.470075 0.116 Uiso 1 1 calc GR . . . .
H1AC H 0.964030 0.122523 0.597904 0.116 Uiso 1 1 calc GR . . . .
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
C7 N1 C14 109.29(15) . . ?
C5 C2 C4 121.05(17) . . ?
C6 C2 C4 120.44(16) . . ?
C6 C2 C5 118.50(17) . . ?
C8 C3 C15 121.95(18) . . ?
C13 C3 C8 118.90(17) . . ?
C13 C3 C15 119.14(18) . . ?
C12 C4 C2 120.79(17) . . ?
C19 C4 C2 121.73(17) . . ?
C19 C4 C12 117.44(17) . . ?
C13 C5 C2 120.72(19) . . ?
C8 C6 C2 120.60(18) . . ?
N1 C7 C12 107.92(16) . . ?
N1 C7 C18 130.04(17) . . ?
C18 C7 C12 122.03(18) . . ?
C6 C8 C3 120.68(18) . . ?
C15 O9 C1AA 117.25(18) . . ?
O10 C11 C14 120.94(18) . . ?
O10 C11 C0AA 120.69(19) . . ?
C14 C11 C0AA 118.35(17) . . ?
C7 C12 C4 119.45(17) . . ?
C16 C12 C4 134.15(17) . . ?
C16 C12 C7 106.39(16) . . ?
C5 C13 C3 120.58(18) . . ?
N1 C14 C11 120.73(16) . . ?
C16 C14 N1 108.76(17) . . ?
C16 C14 C11 130.46(17) . . ?
O9 C15 C3 111.44(18) . . ?
O17 C15 C3 124.9(2) . . ?
O17 C15 O9 123.64(19) . . ?
C14 C16 C12 107.63(16) . . ?
C20 C18 C7 117.47(18) . . ?
C4 C19 C20 121.8(2) . . ?
C18 C20 C19 121.8(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
N1 C7 1.357(3) . ?
N1 C14 1.376(2) . ?
C2 C4 1.483(2) . ?
C2 C5 1.393(3) . ?
C2 C6 1.390(3) . ?
C3 C8 1.387(3) . ?
C3 C13 1.385(3) . ?
C3 C15 1.485(3) . ?
C4 C12 1.417(3) . ?
C4 C19 1.376(3) . ?
C5 C13 1.378(3) . ?
C6 C8 1.379(3) . ?
C7 C12 1.416(2) . ?
C7 C18 1.390(3) . ?
O9 C15 1.338(3) . ?
O9 C1AA 1.436(2) . ?
O10 C11 1.226(2) . ?
C11 C14 1.452(3) . ?
C11 C0AA 1.501(3) . ?
C12 C16 1.414(3) . ?
C14 C16 1.371(3) . ?
C15 O17 1.199(3) . ?
C18 C20 1.365(3) . ?
C19 C20 1.406(3) . ?
