#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/59/4025973.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_4025973
loop_
_publ_author_name
'Xiao-Feng Xia'
'Xing-Zhong Shu'
'Ke-Gong Ji'
'Ali Shaukat'
'Xue-Yuan Liu'
'Yong-Min Liang'
_publ_section_title
;
 Platinum/Scandium-Cocatalyzed Cascade Cyclization and Ring-Opening
 Reaction of Tertiary Amines with Substituted Salicylaldehydes to
 Synthesize 3-(Aminoalkyl)coumarins
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              342
_journal_page_last               345
_journal_paper_doi               10.1021/jo102219z
_journal_volume                  76
_journal_year                    2011
_chemical_formula_sum            'C19 H19 N O3'
_chemical_formula_weight         309.35
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_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                 94.640(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.4632(3)
_cell_length_b                   22.1589(10)
_cell_length_c                   9.6495(4)
_cell_measurement_reflns_used    1682
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      23.37
_cell_measurement_theta_min      2.31
_cell_volume                     1590.57(12)
_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-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω 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  0.0333
_diffrn_reflns_av_sigmaI/netI    0.0352
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            8315
_diffrn_reflns_theta_full        25.27
_diffrn_reflns_theta_max         25.27
_diffrn_reflns_theta_min         1.84
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.9751
_exptl_absorpt_correction_T_min  0.9701
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_description       block
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.29
_refine_diff_density_max         0.136
_refine_diff_density_min         -0.135
_refine_diff_density_rms         0.029
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     213
_refine_ls_number_reflns         2874
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0731
_refine_ls_R_factor_gt           0.0420
_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)+(0.0417P)²+0.2829P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0930
_refine_ls_wR_factor_ref         0.1089
_reflns_number_gt                1911
_reflns_number_total             2874
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo102219z_si_002.cif
_cod_data_source_block           p21n
_cod_database_code               4025973
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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 0.7062(3) -0.04623(8) 0.91389(19) 0.0487(5) Uani 1 1 d .
C2 C 0.8104(3) -0.08094(10) 1.0086(2) 0.0649(6) Uani 1 1 d .
H2 H 0.9313 -0.0721 1.0300 0.078 Uiso 1 1 calc R
C3 C 0.7306(4) -0.12864(10) 1.0700(2) 0.0711(6) Uani 1 1 d .
H3 H 0.7990 -0.1530 1.1325 0.085 Uiso 1 1 calc R
C4 C 0.5514(3) -0.14109(9) 1.0408(2) 0.0676(6) Uani 1 1 d .
H4 H 0.4994 -0.1734 1.0843 0.081 Uiso 1 1 calc R
C5 C 0.4482(3) -0.10597(8) 0.94753(19) 0.0559(5) Uani 1 1 d .
H5 H 0.3267 -0.1145 0.9287 0.067 Uiso 1 1 calc R
C6 C 0.5256(2) -0.05750(8) 0.88088(18) 0.0448(4) Uani 1 1 d .
C7 C 0.4302(2) -0.01985(8) 0.77854(18) 0.0472(5) Uani 1 1 d .
H7 H 0.3088 -0.0270 0.7549 0.057 Uiso 1 1 calc R
C8 C 0.5123(2) 0.02548(8) 0.71615(17) 0.0451(4) Uani 1 1 d .
C9 C 0.7022(3) 0.03678(9) 0.7547(2) 0.0520(5) Uani 1 1 d .
C10 C 0.4275(3) 0.06690(8) 0.60684(19) 0.0533(5) Uani 1 1 d .
H10A H 0.4879 0.0610 0.5226 0.064 Uiso 1 1 calc R
H10B H 0.4506 0.1081 0.6372 0.064 Uiso 1 1 calc R
C11 C 0.2283(3) 0.06035(9) 0.5705(2) 0.0565(5) Uani 1 1 d .
H11A H 0.1641 0.0685 0.6520 0.068 Uiso 1 1 calc R
H11B H 0.2014 0.0193 0.5407 0.068 Uiso 1 1 calc R
C12 C 0.1663(3) 0.10393(9) 0.4550(2) 0.0587(5) Uani 1 1 d .
H12A H 0.2212 0.1430 0.4743 0.070 Uiso 1 1 calc R
H12B H 0.2065 0.0894 0.3679 0.070 Uiso 1 1 calc R
C13 C -0.1079(3) 0.15485(8) 0.35544(19) 0.0496(5) Uani 1 1 d .
C14 C -0.0222(3) 0.18027(9) 0.2466(2) 0.0588(5) Uani 1 1 d .
H14 H 0.0943 0.1687 0.2310 0.071 Uiso 1 1 calc R
C15 C -0.1110(3) 0.22267(9) 0.1619(2) 0.0629(6) Uani 1 1 d .
H15 H -0.0524 0.2393 0.0895 0.076 Uiso 1 1 calc R
C16 C -0.2830(3) 0.24118(9) 0.1806(2) 0.0570(5) Uani 1 1 d .
H16 H -0.3404 0.2698 0.1222 0.068 Uiso 1 1 calc R
C17 C -0.3685(3) 0.21604(8) 0.28919(19) 0.0507(5) Uani 1 1 d .
C18 C -0.2817(3) 0.17369(8) 0.37514(18) 0.0505(5) Uani 1 1 d .
H18 H -0.3405 0.1574 0.4478 0.061 Uiso 1 1 calc R
C19 C -0.6355(3) 0.27408(10) 0.2356(3) 0.0888(8) Uani 1 1 d .
H19A H -0.5708 0.3116 0.2410 0.133 Uiso 1 1 calc R
H19B H -0.7524 0.2799 0.2684 0.133 Uiso 1 1 calc R
H19C H -0.6482 0.2605 0.1409 0.133 Uiso 1 1 calc R
N1 N -0.0261(3) 0.11061(8) 0.4410(2) 0.0642(5) Uani 1 1 d .
O1 O 0.79074(17) 0.00084(6) 0.85231(13) 0.0581(4) Uani 1 1 d .
O2 O 0.78948(19) 0.07674(7) 0.70617(15) 0.0735(4) Uani 1 1 d .
O3 O -0.53972(19) 0.23031(6) 0.31931(15) 0.0715(4) Uani 1 1 d .
H1N H -0.076(3) 0.1040(9) 0.513(2) 0.063(7) Uiso 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 C6 120.61(16)
O1 C1 C2 116.91(18)
C6 C1 C2 122.48(19)
C3 C2 C1 118.2(2)
C3 C2 H2 120.9
C1 C2 H2 120.9
C2 C3 C4 121.1(2)
C2 C3 H3 119.5
C4 C3 H3 119.5
C3 C4 C5 120.3(2)
C3 C4 H4 119.8
C5 C4 H4 119.8
C4 C5 C6 120.3(2)
C4 C5 H5 119.9
C6 C5 H5 119.9
C1 C6 C5 117.61(17)
C1 C6 C7 118.24(16)
C5 C6 C7 124.14(18)
C8 C7 C6 121.54(18)
C8 C7 H7 119.2
C6 C7 H7 119.2
C7 C8 C9 118.90(17)
C7 C8 C10 126.18(18)
C9 C8 C10 114.91(16)
O2 C9 O1 116.58(18)
O2 C9 C8 124.54(19)
O1 C9 C8 118.88(16)
C8 C10 C11 117.24(16)
C8 C10 H10A 108.0
C11 C10 H10A 108.0
C8 C10 H10B 108.0
C11 C10 H10B 108.0
H10A C10 H10B 107.2
C10 C11 C12 110.25(16)
C10 C11 H11A 109.6
C12 C11 H11A 109.6
C10 C11 H11B 109.6
C12 C11 H11B 109.6
H11A C11 H11B 108.1
N1 C12 C11 112.14(17)
N1 C12 H12A 109.2
C11 C12 H12A 109.2
N1 C12 H12B 109.2
C11 C12 H12B 109.2
H12A C12 H12B 107.9
C18 C13 N1 120.00(17)
C18 C13 C14 118.16(17)
N1 C13 C14 121.81(19)
C15 C14 C13 119.7(2)
C15 C14 H14 120.2
C13 C14 H14 120.2
C16 C15 C14 122.33(19)
C16 C15 H15 118.8
C14 C15 H15 118.8
C15 C16 C17 118.16(18)
C15 C16 H16 120.9
C17 C16 H16 120.9
O3 C17 C18 115.51(17)
O3 C17 C16 124.18(18)
C18 C17 C16 120.31(19)
C17 C18 C13 121.38(18)
C17 C18 H18 119.3
C13 C18 H18 119.3
O3 C19 H19A 109.5
O3 C19 H19B 109.5
H19A C19 H19B 109.5
O3 C19 H19C 109.5
H19A C19 H19C 109.5
H19B C19 H19C 109.5
C13 N1 C12 121.00(18)
C13 N1 H1N 114.6(14)
C12 N1 H1N 114.7(15)
C9 O1 C1 121.80(15)
C17 O3 C19 118.23(18)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.378(2)
C1 C6 1.382(2)
C1 C2 1.385(3)
C2 C3 1.371(3)
C2 H2 0.9300
C3 C4 1.372(3)
C3 H3 0.9300
C4 C5 1.377(3)
C4 H4 0.9300
C5 C6 1.400(2)
C5 H5 0.9300
C6 C7 1.437(2)
C7 C8 1.344(2)
C7 H7 0.9300
C8 C9 1.458(3)
C8 C10 1.499(2)
C9 O2 1.215(2)
C9 O1 1.363(2)
C10 C11 1.507(3)
C10 H10A 0.9700
C10 H10B 0.9700
C11 C12 1.518(2)
C11 H11A 0.9700
C11 H11B 0.9700
C12 N1 1.439(3)
C12 H12A 0.9700
C12 H12B 0.9700
C13 C18 1.390(3)
C13 N1 1.391(2)
C13 C14 1.392(3)
C14 C15 1.379(3)
C14 H14 0.9300
C15 C16 1.373(3)
C15 H15 0.9300
C16 C17 1.387(3)
C16 H16 0.9300
C17 O3 1.370(2)
C17 C18 1.379(2)
C18 H18 0.9300
C19 O3 1.418(2)
C19 H19A 0.9600
C19 H19B 0.9600
C19 H19C 0.9600
N1 H1N 0.83(2)
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
O1 C1 C2 C3 -179.05(17)
C6 C1 C2 C3 0.9(3)
C1 C2 C3 C4 -1.3(3)
C2 C3 C4 C5 0.7(3)
C3 C4 C5 C6 0.5(3)
O1 C1 C6 C5 -179.87(16)
C2 C1 C6 C5 0.2(3)
O1 C1 C6 C7 1.5(2)
C2 C1 C6 C7 -178.40(17)
C4 C5 C6 C1 -0.9(3)
C4 C5 C6 C7 177.65(17)
C1 C6 C7 C8 -0.3(3)
C5 C6 C7 C8 -178.84(17)
C6 C7 C8 C9 -0.6(3)
C6 C7 C8 C10 179.00(16)
C7 C8 C9 O2 -179.31(18)
C10 C8 C9 O2 1.1(3)
C7 C8 C9 O1 0.3(2)
C10 C8 C9 O1 -179.31(15)
C7 C8 C10 C11 4.8(3)
C9 C8 C10 C11 -175.57(16)
C8 C10 C11 C12 -177.94(16)
C10 C11 C12 N1 -165.12(17)
C18 C13 C14 C15 -0.3(3)
N1 C13 C14 C15 178.00(18)
C13 C14 C15 C16 0.0(3)
C14 C15 C16 C17 0.1(3)
C15 C16 C17 O3 -179.84(18)
C15 C16 C17 C18 0.0(3)
O3 C17 C18 C13 179.55(16)
C16 C17 C18 C13 -0.3(3)
N1 C13 C18 C17 -177.86(17)
C14 C13 C18 C17 0.5(3)
C18 C13 N1 C12 -159.54(18)
C14 C13 N1 C12 22.2(3)
C11 C12 N1 C13 170.55(17)
O2 C9 O1 C1 -179.47(16)
C8 C9 O1 C1 0.9(2)
C6 C1 O1 C9 -1.8(2)
C2 C1 O1 C9 178.10(17)
C18 C17 O3 C19 179.30(17)
C16 C17 O3 C19 -0.8(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30659334
