#------------------------------------------------------------------------------
#$Date: 2019-11-24 00:41:55 +0200 (Sun, 24 Nov 2019) $
#$Revision: 235814 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/72/4037218.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_4037218
loop_
_publ_author_name
'Rit, Raja K.'
'Ghosh, Koushik'
'Mandal, Rajib'
'Sahoo, Akhila K.'
_publ_section_title
;
 Ruthenium-Catalyzed Intramolecular Hydroarylation of Arenes and
 Mechanistic Study: Synthesis of Dihydrobenzofurans, Indolines, and
 Chromans.
;
_journal_issue                   18
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              8552
_journal_page_last               8560
_journal_paper_doi               10.1021/acs.joc.6b01734
_journal_volume                  81
_journal_year                    2016
_chemical_formula_sum            'C14 H19 N O4'
_chemical_formula_weight         265.30
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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            8
_cell_length_a                   11.1060(5)
_cell_length_b                   10.7491(5)
_cell_length_c                   23.3289(11)
_cell_measurement_reflns_used    1864
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      1.000
_cell_measurement_theta_min      0.8687
_cell_volume                     2785.0(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Mercury v. 1.3 (CCDC)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0411
_diffrn_reflns_av_sigmaI/netI    0.0069
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            131552
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         25.24
_diffrn_reflns_theta_min         2.53
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.8687
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   Sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.256
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.219
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     177
_refine_ls_number_reflns         1853
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0401
_refine_ls_R_factor_gt           0.0377
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0584P)²+1.1810P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1016
_refine_ls_wR_factor_ref         0.1038
_reflns_number_gt                1740
_reflns_number_total             1853
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo6b01734_si_002.cif
_cod_data_source_block           kommu12
_cod_database_code               4037218
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, 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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O4 O 0.78959(11) 0.09333(11) 0.47685(5) 0.0446(4) Uani 1 1 d .
O3 O 0.93731(12) 0.22715(12) 0.53989(5) 0.0475(4) Uani 1 1 d .
O2 O 1.09970(12) 0.48228(12) 0.32797(5) 0.0489(4) Uani 1 1 d .
C7 C 0.87806(13) 0.17980(14) 0.39039(7) 0.0306(4) Uani 1 1 d .
C6 C 0.87203(14) 0.16728(14) 0.44911(7) 0.0317(4) Uani 1 1 d .
C8 C 0.95802(13) 0.25877(14) 0.36261(6) 0.0274(4) Uani 1 1 d .
C9 C 1.03807(13) 0.32799(14) 0.39543(6) 0.0284(4) Uani 1 1 d .
C4 C 1.03314(15) 0.31667(15) 0.45558(7) 0.0323(4) Uani 1 1 d .
H4 H 1.0866 0.3621 0.4780 0.039 Uiso 1 1 calc R
C1 C 0.92872(15) 0.25239(16) 0.29870(7) 0.0352(4) Uani 1 1 d .
C2 C 1.12570(15) 0.41754(15) 0.36914(6) 0.0325(4) Uani 1 1 d .
N1 N 1.23410(14) 0.42418(15) 0.39428(6) 0.0484(5) Uani 1 1 d .
H1 H 1.2505 0.3741 0.4219 0.058 Uiso 1 1 calc R
C5 C 0.95042(15) 0.23949(15) 0.48189(6) 0.0320(4) Uani 1 1 d .
C10 C 1.0080(2) 0.3050(2) 0.57598(8) 0.0620(6) Uani 1 1 d .
H10A H 0.9945 0.3905 0.5660 0.093 Uiso 1 1 calc R
H10B H 1.0917 0.2853 0.5710 0.093 Uiso 1 1 calc R
H10C H 0.9855 0.2918 0.6152 0.093 Uiso 1 1 calc R
C3 C 1.3245(2) 0.5134(2) 0.37619(9) 0.0662(7) Uani 1 1 d .
H3A H 1.2897 0.5952 0.3753 0.099 Uiso 1 1 calc R
H3B H 1.3529 0.4919 0.3386 0.099 Uiso 1 1 calc R
H3C H 1.3906 0.5123 0.4027 0.099 Uiso 1 1 calc R
C13 C 0.84862(18) 0.3625(2) 0.28247(8) 0.0546(5) Uani 1 1 d .
H13A H 0.8246 0.3550 0.2431 0.082 Uiso 1 1 calc R
H13B H 0.8925 0.4386 0.2877 0.082 Uiso 1 1 calc R
H13C H 0.7784 0.3631 0.3065 0.082 Uiso 1 1 calc R
C12 C 1.03630(17) 0.24166(19) 0.25837(7) 0.0498(5) Uani 1 1 d .
H12A H 1.0769 0.3203 0.2563 0.075 Uiso 1 1 calc R
H12B H 1.0089 0.2182 0.2209 0.075 Uiso 1 1 calc R
H12C H 1.0908 0.1796 0.2726 0.075 Uiso 1 1 calc R
C11 C 0.7902(2) -0.03500(19) 0.46164(10) 0.0662(7) Uani 1 1 d .
H11A H 0.8717 -0.0647 0.4605 0.099 Uiso 1 1 calc R
H11B H 0.7538 -0.0452 0.4246 0.099 Uiso 1 1 calc R
H11C H 0.7455 -0.0816 0.4896 0.099 Uiso 1 1 calc R
O6 O 0.80318(10) 0.11624(12) 0.35418(5) 0.0438(4) Uani 1 1 d .
C17 C 0.85673(17) 0.13100(19) 0.29777(7) 0.0453(5) Uani 1 1 d .
H17A H 0.7945 0.1347 0.2687 0.054 Uiso 1 1 calc R
H17B H 0.9093 0.0613 0.2893 0.054 Uiso 1 1 calc R
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
C6 O4 C11 116.08(14)
C5 O3 C10 118.00(14)
O6 C7 C6 122.37(14)
O6 C7 C8 113.95(14)
C6 C7 C8 123.68(14)
O4 C6 C7 123.84(15)
O4 C6 C5 118.65(14)
C7 C6 C5 117.41(14)
C7 C8 C9 118.64(14)
C7 C8 C1 106.96(13)
C9 C8 C1 134.29(14)
C8 C9 C4 118.53(14)
C8 C9 C2 122.23(14)
C4 C9 C2 119.19(14)
C5 C4 C9 121.33(14)
C12 C1 C8 116.02(14)
C12 C1 C13 111.21(15)
C8 C1 C13 109.32(14)
C12 C1 C17 109.64(15)
C8 C1 C17 99.41(13)
C13 C1 C17 110.66(15)
O2 C2 N1 121.74(15)
O2 C2 C9 122.29(15)
N1 C2 C9 115.96(14)
C2 N1 C3 121.94(16)
O3 C5 C4 124.66(15)
O3 C5 C6 114.97(14)
C4 C5 C6 120.37(15)
C7 O6 C17 104.82(12)
O6 C17 C1 107.10(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O4 C6 1.3744(19)
O4 C11 1.424(2)
O3 C5 1.3672(19)
O3 C10 1.424(2)
O2 C2 1.2207(19)
C7 O6 1.3681(19)
C7 C6 1.378(2)
C7 C8 1.389(2)
C6 C5 1.395(2)
C8 C9 1.389(2)
C8 C1 1.528(2)
C9 C4 1.409(2)
C9 C2 1.500(2)
C4 C5 1.382(2)
C1 C12 1.525(2)
C1 C13 1.529(3)
C1 C17 1.530(3)
C2 N1 1.341(2)
N1 C3 1.451(2)
O6 C17 1.453(2)
