#------------------------------------------------------------------------------
#$Date: 2021-07-09 00:31:28 +0300 (Fri, 09 Jul 2021) $
#$Revision: 267403 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/88/4518871.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_4518871
loop_
_publ_author_name
'Medina-Mercado, Ignacio'
'Colin-Molina, Abraham'
'Barquera-Lozada, José Enrique'
'Rodríguez-Molina, Braulio'
'Porcel, Susana'
_publ_contact_author
;
      'Susana Porcel'
      Instituto de Química,
      Universidad Autónoma de México,
      Circuito Exterior,
      Cuidad Universitaria.
      04510 Ciudad de México,
      México  
      
;
_publ_section_title
;
 Gold-Catalyzed Ascorbic Acid-Induced Arylative Carbocyclization of
 Alkynes with Aryldiazonium Tetrafluoroborates
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              8968
_journal_page_last               8977
_journal_paper_doi               10.1021/acscatal.1c01826
_journal_year                    2021
_chemical_formula_sum            'C22 H17 N O4'
_chemical_formula_weight         359.36
_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
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                100.755(4)
_cell_angle_beta                 94.852(3)
_cell_angle_gamma                105.369(3)
_cell_formula_units_Z            2
_cell_length_a                   6.2331(9)
_cell_length_b                   10.6409(16)
_cell_length_c                   14.154(2)
_cell_measurement_reflns_used    2992
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.20
_cell_measurement_theta_min      2.24
_cell_volume                     880.4(2)
_computing_cell_refinement       'APEX3 v2018.1-0(Bruker, 2018)'
_computing_data_collection       'APEX3 v2018.1-0(Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2014)'
_computing_molecular_graphics
'SHELXLe (HÂ¸bschle et al, 2011)'
_computing_publication_material  'CIFTAB V 2013/2 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 52.0833
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type
'Bruker D8 Venture κ geometry diffractometer 208039-1'
_diffrn_measurement_method       'φ and ω-scans'
_diffrn_radiation_monochromator  'Helios multilayer mirror'
_diffrn_radiation_source         'micro-focus X-ray source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1219
_diffrn_reflns_av_unetI/netI     0.1856
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            13375
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_min         2.240
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6459
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Sheldrick, 2012)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_description       platy-prism
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.407
_exptl_crystal_size_mid          0.098
_exptl_crystal_size_min          0.024
_refine_diff_density_max         0.558
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.983
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         4023
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.983
_refine_ls_R_factor_all          0.2369
_refine_ls_R_factor_gt           0.0819
_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)+(0.0849P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1567
_refine_ls_wR_factor_ref         0.2115
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1531
_reflns_number_total             4023
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cs1c01826_si_002.cif
_cod_data_source_block           035RMB20_a
_cod_database_code               4518871
_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   0.963
_shelx_estimated_absorpt_t_max   0.998
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
O001 O 0.2763(5) 0.6121(3) 0.55834(19) 0.0520(8) Uani 1 1 d . . . . .
O1 O 0.2230(5) 0.9834(3) 0.0854(2) 0.0533(8) Uani 1 1 d . . . . .
O003 O 0.5944(6) 0.2858(3) 0.1157(2) 0.0625(10) Uani 1 1 d . . . . .
N3 N 0.7111(7) 0.3898(4) 0.0994(2) 0.0479(10) Uani 1 1 d . . . . .
O2 O 0.8853(6) 0.3968(3) 0.0670(2) 0.0694(10) Uani 1 1 d . . . . .
C006 C 0.2824(6) 0.8780(4) 0.2497(3) 0.0291(9) Uani 1 1 d . . . . .
C007 C 0.2803(6) 0.8108(3) 0.3330(3) 0.0287(9) Uani 1 1 d . . . . .
C008 C 0.3842(6) 0.8446(4) 0.1724(3) 0.0317(10) Uani 1 1 d . . . . .
C009 C 0.3557(6) 0.6068(4) 0.1719(3) 0.0350(10) Uani 1 1 d . . . . .
H009 H 0.217765 0.599773 0.197291 0.042 Uiso 1 1 calc R U . . .
C00A C 0.4317(7) 0.4973(4) 0.1537(3) 0.0346(10) Uani 1 1 d . . . . .
H00A H 0.347214 0.414598 0.165397 0.042 Uiso 1 1 calc R U . . .
C00B C 0.1762(6) 0.9856(4) 0.2520(3) 0.0323(10) Uani 1 1 d . . . . .
C00C C 0.0835(6) 0.7364(4) 0.3573(3) 0.0351(10) Uani 1 1 d . . . . .
H00C H -0.056619 0.730305 0.321855 0.042 Uiso 1 1 calc R U . . .
C00D C 0.4793(6) 0.8207(4) 0.3875(3) 0.0340(10) Uani 1 1 d . . . . .
H00D H 0.615436 0.872849 0.372099 0.041 Uiso 1 1 calc R U . . .
C00E C 0.6306(7) 0.5079(4) 0.1184(3) 0.0329(10) Uani 1 1 d . . . . .
C00F C 0.2914(7) 0.6809(4) 0.4850(3) 0.0365(10) Uani 1 1 d . . . . .
C00G C 0.7527(7) 0.6246(4) 0.0968(3) 0.0397(11) Uani 1 1 d . . . . .
H00G H 0.888806 0.629021 0.070229 0.048 Uiso 1 1 calc R U . . .
C00H C 0.6733(6) 0.7353(4) 0.1145(2) 0.0353(10) Uani 1 1 d . . . . .
H00H H 0.755264 0.816171 0.099323 0.042 Uiso 1 1 calc R U . . .
C00I C 0.4892(7) 0.7572(4) 0.4644(3) 0.0385(11) Uani 1 1 d . . . . .
H00I H 0.628747 0.766353 0.501588 0.046 Uiso 1 1 calc R U . . .
C00J C 0.1512(7) 1.0346(4) 0.1686(3) 0.0400(11) Uani 1 1 d . . . . .
C00K C 0.4754(6) 0.7299(4) 0.1541(3) 0.0311(10) Uani 1 1 d . . . . .
C00L C 0.0859(6) 1.0356(4) 0.3324(3) 0.0395(10) Uani 1 1 d . . . . .
H00L H 0.102558 1.004592 0.390597 0.047 Uiso 1 1 calc R U . . .
C00M C 0.0881(7) 0.6711(4) 0.4323(3) 0.0396(11) Uani 1 1 d . . . . .
H00M H -0.048162 0.619337 0.447924 0.048 Uiso 1 1 calc R U . . .
C00N C -0.0280(7) 1.1303(4) 0.3283(3) 0.0472(12) Uani 1 1 d . . . . .
H00N H -0.090463 1.163352 0.383234 0.057 Uiso 1 1 calc R U . . .
C00O C 0.4049(7) 0.9321(4) 0.0988(3) 0.0427(11) Uani 1 1 d . . . . .
H00B H 0.543677 1.007472 0.119938 0.051 Uiso 1 1 calc R U . . .
H00E H 0.420606 0.879404 0.035603 0.051 Uiso 1 1 calc R U . . .
C00P C 0.0379(7) 1.1293(4) 0.1647(3) 0.0521(12) Uani 1 1 d . . . . .
H00P H 0.021245 1.161511 0.107030 0.062 Uiso 1 1 calc R U . . .
C00Q C -0.0506(7) 1.1764(4) 0.2452(3) 0.0544(13) Uani 1 1 d . . . . .
H00Q H -0.128289 1.241692 0.242965 0.065 Uiso 1 1 calc R U . . .
C00R C 0.4770(8) 0.6271(5) 0.6197(3) 0.0643(14) Uani 1 1 d . . . . .
H00F H 0.586429 0.600435 0.580596 0.096 Uiso 1 1 calc R U . . .
H00J H 0.444555 0.570612 0.667095 0.096 Uiso 1 1 calc R U . . .
H00K H 0.539048 0.720685 0.654046 0.096 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
C00F O001 C00R 117.5(3) . . ?
C00J O1 C00O 115.4(3) . . ?
O2 N3 O003 122.5(4) . . ?
O2 N3 C00E 119.5(4) . . ?
O003 N3 C00E 118.0(4) . . ?
C008 C006 C00B 118.6(3) . . ?
C008 C006 C007 121.8(3) . . ?
C00B C006 C007 119.6(3) . . ?
C00D C007 C00C 118.1(4) . . ?
C00D C007 C006 119.7(3) . . ?
C00C C007 C006 122.2(3) . . ?
C006 C008 C00K 125.0(3) . . ?
C006 C008 C00O 117.3(4) . . ?
C00K C008 C00O 117.7(3) . . ?
C00A C009 C00K 121.8(4) . . ?
C009 C00A C00E 119.0(4) . . ?
C00J C00B C00L 118.2(4) . . ?
C00J C00B C006 118.9(4) . . ?
C00L C00B C006 122.8(4) . . ?
C00M C00C C007 120.7(4) . . ?
C007 C00D C00I 122.4(4) . . ?
C00A C00E C00G 122.0(4) . . ?
C00A C00E N3 118.5(4) . . ?
C00G C00E N3 119.4(4) . . ?
C00I C00F O001 124.3(4) . . ?
C00I C00F C00M 120.7(4) . . ?
O001 C00F C00M 115.0(4) . . ?
C00E C00G C00H 118.7(4) . . ?
C00G C00H C00K 121.0(4) . . ?
C00F C00I C00D 118.1(4) . . ?
O1 C00J C00P 117.6(4) . . ?
O1 C00J C00B 120.9(4) . . ?
C00P C00J C00B 121.3(4) . . ?
C00H C00K C009 117.4(4) . . ?
C00H C00K C008 122.5(3) . . ?
C009 C00K C008 120.0(3) . . ?
C00N C00L C00B 120.4(4) . . ?
C00C C00M C00F 119.9(4) . . ?
C00Q C00N C00L 120.1(4) . . ?
O1 C00O C008 114.0(3) . . ?
C00Q C00P C00J 119.2(4) . . ?
C00N C00Q C00P 120.8(4) . . ?
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
O001 C00F 1.373(4) . ?
O001 C00R 1.416(5) . ?
O1 C00J 1.365(5) . ?
O1 C00O 1.396(4) . ?
O003 N3 1.225(4) . ?
N3 O2 1.203(4) . ?
N3 C00E 1.462(5) . ?
C006 C008 1.349(5) . ?
C006 C00B 1.463(5) . ?
C006 C007 1.488(5) . ?
C007 C00D 1.373(5) . ?
C007 C00C 1.381(5) . ?
C008 C00K 1.468(5) . ?
C008 C00O 1.513(5) . ?
C009 C00A 1.360(5) . ?
C009 C00K 1.405(5) . ?
C00A C00E 1.360(5) . ?
C00B C00J 1.390(5) . ?
C00B C00L 1.391(5) . ?
C00C C00M 1.375(5) . ?
C00D C00I 1.388(5) . ?
C00E C00G 1.376(5) . ?
C00F C00I 1.372(5) . ?
C00F C00M 1.384(5) . ?
C00G C00H 1.384(5) . ?
C00H C00K 1.389(5) . ?
C00J C00P 1.381(5) . ?
C00L C00N 1.385(5) . ?
C00N C00Q 1.366(6) . ?
C00P C00Q 1.376(6) . ?
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
_geom_hbond_publ_flag
C00G H00G O2 0.95 2.51 3.388(5) 153.7 2_765 yes
C00M H00M O001 0.95 2.48 3.291(5) 143.6 2_566 yes
C00O H00E O003 0.99 2.48 3.460(5) 169.5 2_665 yes
