#------------------------------------------------------------------------------
#$Date: 2020-09-06 11:35:09 +0300 (Sun, 06 Sep 2020) $
#$Revision: 256021 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/68/7126837.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_7126837
loop_
_publ_author_name
'Tathe, Akash G.'
'Chintawar, Chetan C.'
'Bhoyare, Vivek W.'
'Patil, Nitin T.'
_publ_section_title
;
 Ligand-enabled gold-catalyzed 1,2-heteroarylation of alkenes.
;
_journal_issue                   65
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              9304
_journal_page_last               9307
_journal_paper_doi               10.1039/d0cc03707a
_journal_volume                  56
_journal_year                    2020
_chemical_formula_moiety         'C19 H19 N O4'
_chemical_formula_sum            'C19 H19 N O4'
_chemical_formula_weight         325.35
_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
_audit_update_record
;
2019-12-19 deposited with the CCDC.	2020-07-07 downloaded from the CCDC.
;
_cell_angle_alpha                81.614(2)
_cell_angle_beta                 79.942(2)
_cell_angle_gamma                89.931(2)
_cell_formula_units_Z            2
_cell_length_a                   7.7313(4)
_cell_length_b                   8.2310(4)
_cell_length_c                   13.2902(7)
_cell_measurement_reflns_used    7054
_cell_measurement_temperature    140(2)
_cell_measurement_theta_max      29.49
_cell_measurement_theta_min      2.50
_cell_volume                     823.58(7)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      140(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0434
_diffrn_reflns_av_unetI/netI     0.0394
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            16074
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.868
_diffrn_reflns_theta_min         2.502
_exptl_absorpt_coefficient_mu    0.092
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_description       rectangular
_exptl_crystal_F_000             344.0
_refine_diff_density_max         0.438
_refine_diff_density_min         -0.343
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3916
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0743
_refine_ls_R_factor_gt           0.0506
_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)+(0.0612P)²+0.3563P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1202
_refine_ls_wR_factor_ref         0.1324
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2966
_reflns_number_total             3916
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0cc03707a2.cif
_cod_data_source_block           shelx
_cod_depositor_comments          'Adding full bibliography for 7126837.cif.'
_cod_database_code               7126837
_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.
;
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 0.78777(15) 0.94693(14) 0.18463(9) 0.0291(3) Uani 1 1 d . . . . .
O002 O 0.70785(16) 0.88162(13) -0.03906(9) 0.0301(3) Uani 1 1 d . . . . .
O003 O 0.52173(16) 0.46712(15) 0.22721(9) 0.0326(3) Uani 1 1 d . . . . .
O004 O 0.03342(17) 0.58849(17) 0.62825(10) 0.0406(3) Uani 1 1 d . . . . .
N005 N 0.59944(17) 0.70306(16) 0.11057(10) 0.0231(3) Uani 1 1 d . . . . .
C006 C 0.7557(2) 0.58688(18) -0.02356(12) 0.0218(3) Uani 1 1 d . . . . .
C007 C 0.6952(2) 0.46043(19) 0.05602(12) 0.0226(3) Uani 1 1 d . . . . .
C008 C 0.5945(2) 0.53385(19) 0.14334(12) 0.0233(3) Uani 1 1 d . . . . .
C009 C 0.6371(2) 0.86449(19) 0.24824(12) 0.0238(3) Uani 1 1 d . . . . .
H009 H 0.674450 0.761117 0.287325 0.029 Uiso 1 1 calc R U . . .
C00A C 0.6908(2) 0.74459(19) 0.00937(12) 0.0225(3) Uani 1 1 d . . . . .
C00B C 0.8616(2) 0.5573(2) -0.11328(13) 0.0282(4) Uani 1 1 d . . . . .
H00B H 0.903108 0.644079 -0.167555 0.034 Uiso 1 1 calc R U . . .
C00C C 0.7366(2) 0.2989(2) 0.04823(14) 0.0295(4) Uani 1 1 d . . . . .
H00C H 0.693754 0.212448 0.102406 0.035 Uiso 1 1 calc R U . . .
C00D C 0.9054(2) 0.3948(2) -0.12113(15) 0.0341(4) Uani 1 1 d . . . . .
H00D H 0.979097 0.370327 -0.181800 0.041 Uiso 1 1 calc R U . . .
C00E C 0.8435(2) 0.2682(2) -0.04219(15) 0.0344(4) Uani 1 1 d . . . . .
H00E H 0.874664 0.158471 -0.050047 0.041 Uiso 1 1 calc R U . . .
C00F C 0.5412(2) 0.9702(2) 0.32535(13) 0.0300(4) Uani 1 1 d . . . . .
H00A H 0.628169 1.018188 0.359895 0.036 Uiso 1 1 calc R U . . .
H00F H 0.484930 1.061825 0.287229 0.036 Uiso 1 1 calc R U . . .
C00G C 0.2259(2) 0.8973(2) 0.40779(14) 0.0305(4) Uani 1 1 d . . . . .
H00G H 0.190224 0.978005 0.357252 0.037 Uiso 1 1 calc R U . . .
C00H C 0.5189(2) 0.8202(2) 0.17564(13) 0.0264(4) Uani 1 1 d . . . . .
H00H H 0.406460 0.772671 0.216826 0.032 Uiso 1 1 calc R U . . .
H00I H 0.492422 0.921241 0.131269 0.032 Uiso 1 1 calc R U . . .
C00I C 0.0977(2) 0.8064(2) 0.48065(14) 0.0320(4) Uani 1 1 d . . . . .
H00Z H -0.023330 0.825047 0.479649 0.038 Uiso 1 1 calc R U . . .
C00J C 0.4030(2) 0.8742(2) 0.40641(12) 0.0260(4) Uani 1 1 d . . . . .
C00K C 0.3256(2) 0.6650(2) 0.55622(13) 0.0323(4) Uani 1 1 d . . . . .
H00K H 0.361148 0.585779 0.607631 0.039 Uiso 1 1 calc R U . . .
C00L C 0.1481(2) 0.6886(2) 0.55456(12) 0.0293(4) Uani 1 1 d . . . . .
C00M C 0.4503(2) 0.7568(2) 0.48312(13) 0.0303(4) Uani 1 1 d . . . . .
H00M H 0.571244 0.739643 0.485028 0.036 Uiso 1 1 calc R U . . .
C00N C 0.9280(2) 0.9701(2) 0.23773(15) 0.0363(4) Uani 1 1 d . . . . .
H00J H 1.026631 1.027329 0.189160 0.054 Uiso 1 1 calc R U . . .
H00L H 0.888250 1.035814 0.292838 0.054 Uiso 1 1 calc R U . . .
H00N H 0.965955 0.862982 0.267843 0.054 Uiso 1 1 calc R U . . .
C00O C -0.1488(3) 0.5985(3) 0.62128(16) 0.0425(5) Uani 1 1 d . . . . .
H00O H -0.217220 0.522022 0.677547 0.064 Uiso 1 1 calc R U . . .
H00P H -0.187739 0.710715 0.626761 0.064 Uiso 1 1 calc R U . . .
H00Q H -0.166433 0.569592 0.554750 0.064 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
C00N O001 C009 114.16(13) . . ?
C00L O004 C00O 116.88(15) . . ?
C008 N005 C00A 112.01(13) . . ?
C008 N005 C00H 123.09(13) . . ?
C00A N005 C00H 124.91(13) . . ?
C00B C006 C007 121.54(15) . . ?
C00B C006 C00A 130.15(14) . . ?
C007 C006 C00A 108.28(14) . . ?
C00C C007 C006 121.53(15) . . ?
C00C C007 C008 130.28(15) . . ?
C006 C007 C008 108.12(13) . . ?
O003 C008 N005 124.69(15) . . ?
O003 C008 C007 129.36(15) . . ?
N005 C008 C007 105.96(13) . . ?
O001 C009 C00H 106.38(13) . . ?
O001 C009 C00F 112.29(13) . . ?
C00H C009 C00F 111.26(14) . . ?
O001 C009 H009 108.9 . . ?
C00H C009 H009 108.9 . . ?
C00F C009 H009 108.9 . . ?
O002 C00A N005 125.44(15) . . ?
O002 C00A C006 128.98(15) . . ?
N005 C00A C006 105.57(13) . . ?
C006 C00B C00D 117.18(16) . . ?
C006 C00B H00B 121.4 . . ?
C00D C00B H00B 121.4 . . ?
C007 C00C C00E 117.23(16) . . ?
C007 C00C H00C 121.4 . . ?
C00E C00C H00C 121.4 . . ?
C00E C00D C00B 121.35(16) . . ?
C00E C00D H00D 119.3 . . ?
C00B C00D H00D 119.3 . . ?
C00D C00E C00C 121.15(16) . . ?
C00D C00E H00E 119.4 . . ?
C00C C00E H00E 119.4 . . ?
C00J C00F C009 112.79(13) . . ?
C00J C00F H00A 109.0 . . ?
C009 C00F H00A 109.0 . . ?
C00J C00F H00F 109.0 . . ?
C009 C00F H00F 109.0 . . ?
H00A C00F H00F 107.8 . . ?
C00J C00G C00I 122.23(17) . . ?
C00J C00G H00G 118.9 . . ?
C00I C00G H00G 118.9 . . ?
N005 C00H C009 112.09(13) . . ?
N005 C00H H00H 109.2 . . ?
C009 C00H H00H 109.2 . . ?
N005 C00H H00I 109.2 . . ?
C009 C00H H00I 109.2 . . ?
H00H C00H H00I 107.9 . . ?
C00L C00I C00G 119.37(16) . . ?
C00L C00I H00I 120.3 . . ?
C00G C00I H00I 120.3 . . ?
C00G C00J C00M 117.23(16) . . ?
C00G C00J C00F 121.92(16) . . ?
C00M C00J C00F 120.85(16) . . ?
C00M C00K C00L 119.92(16) . . ?
C00M C00K H00K 120.0 . . ?
C00L C00K H00K 120.0 . . ?
O004 C00L C00I 124.44(16) . . ?
O004 C00L C00K 115.95(16) . . ?
C00I C00L C00K 119.60(16) . . ?
C00K C00M C00J 121.63(16) . . ?
C00K C00M H00M 119.2 . . ?
C00J C00M H00M 119.2 . . ?
O001 C00N H00J 109.5 . . ?
O001 C00N H00L 109.5 . . ?
H00J C00N H00L 109.5 . . ?
O001 C00N H00N 109.5 . . ?
H00J C00N H00N 109.5 . . ?
H00L C00N H00N 109.5 . . ?
O004 C00O H00O 109.5 . . ?
O004 C00O H00P 109.5 . . ?
H00O C00O H00P 109.5 . . ?
O004 C00O H00Q 109.5 . . ?
H00O C00O H00Q 109.5 . . ?
H00P C00O H00Q 109.5 . . ?
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 C00N 1.420(2) . ?
O001 C009 1.4222(19) . ?
O002 C00A 1.2095(19) . ?
O003 C008 1.2099(19) . ?
O004 C00L 1.374(2) . ?
O004 C00O 1.430(2) . ?
N005 C008 1.396(2) . ?
N005 C00A 1.400(2) . ?
N005 C00H 1.456(2) . ?
C006 C00B 1.376(2) . ?
C006 C007 1.389(2) . ?
C006 C00A 1.488(2) . ?
C007 C00C 1.381(2) . ?
C007 C008 1.485(2) . ?
C009 C00H 1.520(2) . ?
C009 C00F 1.533(2) . ?
C009 H009 1.0000 . ?
C00B C00D 1.393(2) . ?
C00B H00B 0.9500 . ?
C00C C00E 1.390(3) . ?
C00C H00C 0.9500 . ?
C00D C00E 1.387(3) . ?
C00D H00D 0.9500 . ?
C00E H00E 0.9500 . ?
C00F C00J 1.510(2) . ?
C00F H00A 0.9900 . ?
C00F H00F 0.9900 . ?
C00G C00J 1.379(2) . ?
C00G C00I 1.391(2) . ?
C00G H00G 0.9500 . ?
C00H H00H 0.9900 . ?
C00H H00I 0.9900 . ?
C00I C00L 1.383(3) . ?
C00I H00I 0.9500 . ?
C00J C00M 1.396(2) . ?
C00K C00M 1.380(2) . ?
C00K C00L 1.390(3) . ?
C00K H00K 0.9500 . ?
C00M H00M 0.9500 . ?
C00N H00J 0.9800 . ?
C00N H00L 0.9800 . ?
C00N H00N 0.9800 . ?
C00O H00O 0.9800 . ?
C00O H00P 0.9800 . ?
C00O H00Q 0.9800 . ?
