#------------------------------------------------------------------------------
#$Date: 2019-10-28 11:03:00 +0200 (Mon, 28 Oct 2019) $
#$Revision: 219957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/47/4514797.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_4514797
loop_
_publ_author_name
'Sahani, Rajkumar Lalji'
'Liu, Rai-Shung'
_publ_section_title
;
 Gold-Catalyzed Oxidative Arylations of 3-Butyn-1-ols and 2-Propyn-1-ols
 with Nitrones to Yield Distinct Fused Indoles Bearing a Heterocyclic Ring
;
_journal_issue                   7
_journal_name_full               'ACS Catalysis'
_journal_page_first              5890
_journal_paper_doi               10.1021/acscatal.9b01491
_journal_volume                  9
_journal_year                    2019
_chemical_formula_moiety         'C22 H23 N O'
_chemical_formula_sum            'C22 H23 N O'
_chemical_formula_weight         317.41
_space_group_IT_number           78
_space_group_name_Hall           'P 4cw'
_space_group_name_H-M_alt        'P 43'
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_Hall  'P 4cw'
_symmetry_space_group_name_H-M   'P 43'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.6545(5)
_cell_length_b                   10.6545(5)
_cell_length_c                   15.1128(7)
_cell_measurement_reflns_used    5451
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      24.997
_cell_measurement_theta_min      3.021
_cell_volume                     1715.58(14)
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2005)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'D8 Venture'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0351
_diffrn_reflns_av_sigmaI/netI    0.0393
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7821
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         3.02
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  0.9595
_exptl_absorpt_correction_T_min  0.9435
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.229
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.79
_exptl_crystal_size_mid          0.75
_exptl_crystal_size_min          0.56
_refine_diff_density_max         0.101
_refine_diff_density_min         -0.097
_refine_diff_density_rms         0.021
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.5(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2956
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0348
_refine_ls_R_factor_gt           0.0309
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0226P)²+0.2479P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0692
_refine_ls_wR_factor_ref         0.0717
_reflns_number_gt                2765
_reflns_number_total             2956
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cs9b01491_si_002.cif
_cod_data_source_block           d20324a
_cod_database_code               4514797
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y, x, z+3/4'
'y, -x, z+1/4'
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.72250(14) 0.66900(15) 0.38195(9) 0.0312(3) Uani 1 1 d .
C2 C 0.78930(16) 0.59378(15) 0.31013(10) 0.0391(4) Uani 1 1 d .
H2A H 0.8247 0.5166 0.3367 0.047 Uiso 1 1 calc R
H2B H 0.7273 0.5682 0.2648 0.047 Uiso 1 1 calc R
C3 C 0.89456(17) 0.66720(18) 0.26548(11) 0.0452(4) Uani 1 1 d .
H3A H 0.9630 0.6816 0.3086 0.054 Uiso 1 1 calc R
H3B H 0.9291 0.6169 0.2160 0.054 Uiso 1 1 calc R
C4 C 0.84899(18) 0.79275(18) 0.23016(11) 0.0486(5) Uani 1 1 d .
H4A H 0.7877 0.7785 0.1820 0.058 Uiso 1 1 calc R
H4B H 0.9208 0.8400 0.2054 0.058 Uiso 1 1 calc R
C5 C 0.78762(17) 0.86949(16) 0.30343(11) 0.0417(4) Uani 1 1 d .
H5A H 0.7550 0.9491 0.2787 0.050 Uiso 1 1 calc R
H5B H 0.8507 0.8902 0.3492 0.050 Uiso 1 1 calc R
C6 C 0.68020(15) 0.79539(15) 0.34508(10) 0.0334(4) Uani 1 1 d .
H6A H 0.6428 0.8456 0.3935 0.040 Uiso 1 1 calc R
H6B H 0.6143 0.7812 0.3000 0.040 Uiso 1 1 calc R
C7 C 0.61151(15) 0.59464(15) 0.41924(10) 0.0337(3) Uani 1 1 d .
H7A H 0.5399 0.5982 0.3776 0.040 Uiso 1 1 calc R
H7B H 0.6356 0.5056 0.4274 0.040 Uiso 1 1 calc R
C8 C 0.57489(14) 0.65028(14) 0.50562(9) 0.0292(3) Uani 1 1 d .
C9 C 0.46288(14) 0.70043(15) 0.62577(9) 0.0310(3) Uani 1 1 d .
C10 C 0.37203(16) 0.71166(18) 0.69135(11) 0.0436(4) Uani 1 1 d .
H10 H 0.2943 0.6683 0.6874 0.052 Uiso 1 1 calc R
C11 C 0.39915(18) 0.78800(18) 0.76217(12) 0.0519(5) Uani 1 1 d .
H11 H 0.3389 0.7966 0.8081 0.062 Uiso 1 1 calc R
C12 C 0.51270(17) 0.85335(17) 0.76863(11) 0.0473(4) Uani 1 1 d .
H12 H 0.5278 0.9060 0.8183 0.057 Uiso 1 1 calc R
C13 C 0.60287(16) 0.84222(15) 0.70379(10) 0.0375(4) Uani 1 1 d .
H13 H 0.6799 0.8867 0.7083 0.045 Uiso 1 1 calc R
C14 C 0.57922(14) 0.76438(14) 0.63115(9) 0.0292(3) Uani 1 1 d .
C15 C 0.64891(13) 0.72828(14) 0.55368(9) 0.0281(3) Uani 1 1 d .
C16 C 0.77800(13) 0.76462(14) 0.52317(9) 0.0280(3) Uani 1 1 d .
H16 H 0.7751 0.8530 0.5011 0.034 Uiso 1 1 calc R
C17 C 0.87673(13) 0.75623(14) 0.59526(10) 0.0285(3) Uani 1 1 d .
C18 C 0.86909(15) 0.66759(16) 0.66170(11) 0.0371(4) Uani 1 1 d .
H18 H 0.8044 0.6062 0.6600 0.045 Uiso 1 1 calc R
C19 C 0.95434(16) 0.66690(19) 0.73073(11) 0.0470(5) Uani 1 1 d .
H19 H 0.9475 0.6061 0.7765 0.056 Uiso 1 1 calc R
C20 C 1.04864(17) 0.7541(2) 0.73286(12) 0.0514(5) Uani 1 1 d .
H20 H 1.1062 0.7549 0.7809 0.062 Uiso 1 1 calc R
C21 C 1.06041(17) 0.84099(19) 0.66552(14) 0.0516(5) Uani 1 1 d .
H21 H 1.1278 0.8994 0.6660 0.062 Uiso 1 1 calc R
C22 C 0.97356(15) 0.84263(16) 0.59721(12) 0.0399(4) Uani 1 1 d .
H22 H 0.9806 0.9034 0.5515 0.048 Uiso 1 1 calc R
N1 N 0.46197(11) 0.63218(11) 0.54834(8) 0.0313(3) Uani 1 1 d .
H1 H 0.3945 0.5804 0.5271 0.038 Uiso 1 1 d R
O1 O 0.81566(9) 0.68432(10) 0.45136(6) 0.0305(3) 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
O1 C1 C2 104.71(12)
O1 C1 C6 111.48(12)
C2 C1 C6 109.98(12)
O1 C1 C7 108.66(11)
C2 C1 C7 110.51(13)
C6 C1 C7 111.29(13)
C3 C2 C1 112.86(13)
C3 C2 H2A 109.0
C1 C2 H2A 109.0
C3 C2 H2B 109.0
C1 C2 H2B 109.0
H2A C2 H2B 107.8
C4 C3 C2 111.84(14)
C4 C3 H3A 109.2
C2 C3 H3A 109.2
C4 C3 H3B 109.2
C2 C3 H3B 109.2
H3A C3 H3B 107.9
C3 C4 C5 110.74(13)
C3 C4 H4A 109.5
C5 C4 H4A 109.5
C3 C4 H4B 109.5
C5 C4 H4B 109.5
H4A C4 H4B 108.1
C4 C5 C6 110.11(14)
C4 C5 H5A 109.6
C6 C5 H5A 109.6
C4 C5 H5B 109.6
C6 C5 H5B 109.6
H5A C5 H5B 108.2
C1 C6 C5 112.69(13)
C1 C6 H6A 109.1
C5 C6 H6A 109.1
C1 C6 H6B 109.1
C5 C6 H6B 109.1
H6A C6 H6B 107.8
C8 C7 C1 108.65(12)
C8 C7 H7A 110.0
C1 C7 H7A 110.0
C8 C7 H7B 110.0
C1 C7 H7B 110.0
H7A C7 H7B 108.3
C15 C8 N1 110.01(13)
C15 C8 C7 124.21(13)
N1 C8 C7 125.78(13)
N1 C9 C10 130.23(15)
N1 C9 C14 107.98(12)
C10 C9 C14 121.79(14)
C11 C10 C9 117.35(16)
C11 C10 H10 121.3
C9 C10 H10 121.3
C10 C11 C12 122.03(16)
C10 C11 H11 119.0
C12 C11 H11 119.0
C13 C12 C11 120.70(16)
C13 C12 H12 119.6
C11 C12 H12 119.7
C12 C13 C14 118.93(15)
C12 C13 H13 120.5
C14 C13 H13 120.5
C13 C14 C9 119.20(14)
C13 C14 C15 134.76(14)
C9 C14 C15 106.04(12)
C8 C15 C14 107.42(13)
C8 C15 C16 121.74(13)
C14 C15 C16 130.82(13)
O1 C16 C15 109.50(11)
O1 C16 C17 108.25(11)
C15 C16 C17 113.55(12)
O1 C16 H16 108.5
C15 C16 H16 108.5
C17 C16 H16 108.5
C18 C17 C22 118.93(14)
C18 C17 C16 121.44(13)
C22 C17 C16 119.56(14)
C17 C18 C19 120.88(15)
C17 C18 H18 119.6
C19 C18 H18 119.6
C20 C19 C18 119.75(17)
C20 C19 H19 120.1
C18 C19 H19 120.1
C19 C20 C21 120.27(16)
C19 C20 H20 119.9
C21 C20 H20 119.9
C20 C21 C22 119.76(17)
C20 C21 H21 120.1
C22 C21 H21 120.1
C17 C22 C21 120.35(17)
C17 C22 H22 119.8
C21 C22 H22 119.8
C9 N1 C8 108.52(12)
C9 N1 H1 126.3
C8 N1 H1 125.2
C16 O1 C1 114.88(10)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.4534(17)
C1 C2 1.525(2)
C1 C6 1.525(2)
C1 C7 1.531(2)
C2 C3 1.525(2)
C2 H2A 0.9900
C2 H2B 0.9900
C3 C4 1.520(3)
C3 H3A 0.9900
C3 H3B 0.9900
C4 C5 1.524(2)
C4 H4A 0.9900
C4 H4B 0.9900
C5 C6 1.526(2)
C5 H5A 0.9900
C5 H5B 0.9900
C6 H6A 0.9900
C6 H6B 0.9900
C7 C8 1.486(2)
C7 H7A 0.9900
C7 H7B 0.9900
C8 C15 1.356(2)
C8 N1 1.3789(19)
C9 N1 1.378(2)
C9 C10 1.391(2)
C9 C14 1.417(2)
C10 C11 1.375(3)
C10 H10 0.9500
C11 C12 1.399(3)
C11 H11 0.9500
C12 C13 1.377(2)
C12 H12 0.9500
C13 C14 1.399(2)
C13 H13 0.9500
C14 C15 1.4387(19)
C15 C16 1.501(2)
C16 O1 1.4389(16)
C16 C17 1.517(2)
C16 H16 1.0000
C17 C18 1.381(2)
C17 C22 1.383(2)
C18 C19 1.383(2)
C18 H18 0.9500
C19 C20 1.369(3)
C19 H19 0.9500
C20 C21 1.381(3)
C20 H20 0.9500
C21 C22 1.386(2)
C21 H21 0.9500
C22 H22 0.9500
N1 H1 0.9608
