#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:56:42 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178451 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/72/4027224.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_4027224
loop_
_publ_author_name
'Veerababurao Kavala'
'Cheng-Chuan Wang'
'Deepak Kumar Barange'
'Chun-Wei Kuo'
'Po-Min Lei'
'Ching-Fa Yao'
_publ_section_title
;
 Synthesis of Isocoumarin Derivatives via the Copper-Catalyzed Tandem
 Sequential Cyclization of 2- Halo-N-phenyl Benzamides and Acyclic
 1,3-Diketones
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5022
_journal_page_last               5029
_journal_paper_doi               10.1021/jo300501j
_journal_volume                  77
_journal_year                    2012
_chemical_formula_moiety         'C75 H48 O10'
_chemical_formula_sum            'C75 H48 O10'
_chemical_formula_weight         1109.13
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                109.783(2)
_cell_angle_beta                 96.555(2)
_cell_angle_gamma                95.722(2)
_cell_formula_units_Z            1
_cell_length_a                   7.5014(3)
_cell_length_b                   11.7780(5)
_cell_length_c                   16.6978(6)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      0
_cell_measurement_theta_min      0
_cell_volume                     1363.95(10)
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Giacovazzo et al, 1993)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_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  0.0280
_diffrn_reflns_av_sigmaI/netI    0.0328
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            14097
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         1.31
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.9938
_exptl_absorpt_correction_T_min  0.9669
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_description       prism
_exptl_crystal_F_000             578
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.242
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.246
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     397
_refine_ls_number_reflns         4756
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.246
_refine_ls_R_factor_all          0.0847
_refine_ls_R_factor_gt           0.0739
_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)+(0.0030P)²+2.6208P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1633
_refine_ls_wR_factor_ref         0.1674
_reflns_number_gt                3982
_reflns_number_total             4756
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo300501j_si_003.cif
_cod_data_source_block           a12808
_cod_original_cell_volume        1363.95(9)
_cod_database_code               4027224
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.2649(5) 1.0150(3) 0.1643(2) 0.0352(8) Uani 1 1 d .
C2 C 0.3575(5) 1.1333(3) 0.1712(2) 0.0330(8) Uani 1 1 d .
C3 C 0.4327(5) 1.2195(3) 0.2523(2) 0.0387(9) Uani 1 1 d .
H3 H 0.4236 1.2007 0.3029 0.046 Uiso 1 1 calc R
C4 C 0.5195(5) 1.3314(4) 0.2585(3) 0.0440(9) Uani 1 1 d .
H4 H 0.5699 1.3901 0.3135 0.053 Uiso 1 1 calc R
C5 C 0.5338(5) 1.3586(3) 0.1848(3) 0.0431(9) Uani 1 1 d .
H5 H 0.5931 1.4363 0.1897 0.052 Uiso 1 1 calc R
C6 C 0.4628(5) 1.2741(3) 0.1042(3) 0.0427(9) Uani 1 1 d .
H6 H 0.4755 1.2934 0.0542 0.051 Uiso 1 1 calc R
C7 C 0.3720(5) 1.1600(3) 0.0961(2) 0.0340(8) Uani 1 1 d .
C8 C 0.2971(5) 1.0683(3) 0.0146(2) 0.0371(8) Uani 1 1 d .
H8 H 0.3057 1.0855 -0.0366 0.044 Uiso 1 1 calc R
C9 C 0.2152(5) 0.9589(3) 0.0086(2) 0.0322(8) Uani 1 1 d .
C10 C 0.1356(5) 0.8547(3) -0.0696(2) 0.0321(8) Uani 1 1 d .
C11 C 0.1401(5) 0.8636(3) -0.1512(2) 0.0382(9) Uani 1 1 d .
H11 H 0.1937 0.9376 -0.1553 0.046 Uiso 1 1 calc R
C12 C 0.0676(5) 0.7661(3) -0.2256(2) 0.0425(9) Uani 1 1 d .
H12 H 0.0720 0.7735 -0.2803 0.051 Uiso 1 1 calc R
C13 C -0.0109(5) 0.6585(3) -0.2206(2) 0.0428(9) Uani 1 1 d .
H13 H -0.0615 0.5918 -0.2718 0.051 Uiso 1 1 calc R
C14 C -0.0159(5) 0.6478(3) -0.1409(3) 0.0444(9) Uani 1 1 d .
H14 H -0.0700 0.5736 -0.1374 0.053 Uiso 1 1 calc R
C15 C 0.0577(5) 0.7449(3) -0.0662(2) 0.0412(9) Uani 1 1 d .
H15 H 0.0548 0.7362 -0.0118 0.049 Uiso 1 1 calc R
C16 C 0.7258(5) 1.1028(3) 0.4305(2) 0.0372(8) Uani 1 1 d .
C17 C 0.7012(5) 1.1908(3) 0.5129(2) 0.0344(8) Uani 1 1 d .
C18 C 0.6674(5) 1.3069(3) 0.5173(3) 0.0423(9) Uani 1 1 d .
H18 H 0.6594 1.3282 0.4672 0.051 Uiso 1 1 calc R
C19 C 0.6455(6) 1.3911(4) 0.5958(3) 0.0520(11) Uani 1 1 d .
H19 H 0.6227 1.4705 0.5996 0.062 Uiso 1 1 calc R
C20 C 0.6571(6) 1.3588(4) 0.6685(3) 0.0572(12) Uani 1 1 d .
H20 H 0.6423 1.4169 0.7220 0.069 Uiso 1 1 calc R
C21 C 0.6895(5) 1.2444(4) 0.6648(3) 0.0469(10) Uani 1 1 d .
H21 H 0.6967 1.2239 0.7153 0.056 Uiso 1 1 calc R
C22 C 0.7120(5) 1.1581(3) 0.5863(2) 0.0362(8) Uani 1 1 d .
C23 C 0.7449(5) 1.0367(3) 0.5780(2) 0.0378(8) Uani 1 1 d .
H23 H 0.7512 1.0129 0.6271 0.045 Uiso 1 1 calc R
C24 C 0.7665(5) 0.9574(3) 0.5023(2) 0.0320(8) Uani 1 1 d .
C25 C 0.8008(5) 0.8299(3) 0.4825(2) 0.0330(8) Uani 1 1 d .
C26 C 0.8139(5) 0.7565(3) 0.3995(2) 0.0392(9) Uani 1 1 d .
H26 H 0.8042 0.7889 0.3545 0.047 Uiso 1 1 calc R
C27 C 0.8408(5) 0.6369(3) 0.3813(3) 0.0465(10) Uani 1 1 d .
H27 H 0.8479 0.5872 0.3239 0.056 Uiso 1 1 calc R
C28 C 0.8575(5) 0.5891(4) 0.4462(3) 0.0495(11) Uani 1 1 d .
H28 H 0.8757 0.5066 0.4334 0.059 Uiso 1 1 calc R
C29 C 0.8477(6) 0.6611(4) 0.5296(3) 0.0507(11) Uani 1 1 d .
H29 H 0.8607 0.6284 0.5744 0.061 Uiso 1 1 calc R
C30 C 0.8189(5) 0.7816(4) 0.5481(3) 0.0428(9) Uani 1 1 d .
H30 H 0.8115 0.8310 0.6055 0.051 Uiso 1 1 calc R
C31 C 0.8221(9) 0.5537(6) 0.0357(5) 0.0317(15) Uani 0.50 1 d P
C32 C 0.7712(5) 0.6555(3) 0.1001(3) 0.0415(9) Uani 1 1 d .
C33 C 0.8847(5) 0.7576(4) 0.1594(3) 0.0446(9) Uani 1 1 d .
H33 H 1.0125 0.7597 0.1649 0.054 Uiso 1 1 calc R
C34 C 0.8136(5) 0.8546(3) 0.2096(2) 0.0378(9) Uani 1 1 d .
H34 H 0.8918 0.9237 0.2499 0.045 Uiso 1 1 calc R
C35 C 0.6272(5) 0.8518(3) 0.2018(2) 0.0385(9) Uani 1 1 d .
H35 H 0.5780 0.9192 0.2369 0.046 Uiso 1 1 calc R
C36 C 0.5120(5) 0.7516(3) 0.1431(2) 0.0387(9) Uani 1 1 d .
H36 H 0.3845 0.7511 0.1377 0.046 Uiso 1 1 calc R
C37 C 0.5829(5) 0.6515(3) 0.0921(2) 0.0349(8) Uani 1 1 d .
C38 C 0.4665(6) 0.5457(3) 0.0279(2) 0.0465(10) Uani 1 1 d .
O1 O 0.2397(4) 0.9816(2) 0.22405(16) 0.0468(7) Uani 1 1 d .
O2 O 0.1996(3) 0.9329(2) 0.08303(15) 0.0361(6) Uani 1 1 d .
O3 O 0.7225(4) 1.1205(2) 0.36304(17) 0.0521(8) Uani 1 1 d .
O4 O 0.7572(3) 0.9896(2) 0.42930(14) 0.0358(6) Uani 1 1 d .
O5 O 0.9782(7) 0.5405(5) 0.0297(3) 0.0430(12) Uani 0.50 1 d P
O6 O 0.6939(6) 0.4610(4) -0.0242(3) 0.0291(10) Uani 0.50 1 d P
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'
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
O1 C1 O2 116.5(3) . .
O1 C1 C2 126.1(3) . .
O2 C1 C2 117.3(3) . .
C3 C2 C7 120.4(3) . .
C3 C2 C1 120.0(3) . .
C7 C2 C1 119.7(3) . .
C4 C3 C2 119.8(4) . .
C4 C3 H3 120.1 . .
C2 C3 H3 120.1 . .
C3 C4 C5 120.2(4) . .
C3 C4 H4 119.9 . .
C5 C4 H4 119.9 . .
C6 C5 C4 120.8(4) . .
C6 C5 H5 119.6 . .
C4 C5 H5 119.6 . .
C5 C6 C7 120.2(4) . .
C5 C6 H6 119.9 . .
C7 C6 H6 119.9 . .
C6 C7 C2 118.6(3) . .
C6 C7 C8 122.9(3) . .
C2 C7 C8 118.4(3) . .
C9 C8 C7 121.7(3) . .
C9 C8 H8 119.2 . .
C7 C8 H8 119.2 . .
C8 C9 O2 119.8(3) . .
C8 C9 C10 128.3(3) . .
O2 C9 C10 111.9(3) . .
C15 C10 C11 117.9(3) . .
C15 C10 C9 122.0(3) . .
C11 C10 C9 120.0(3) . .
C12 C11 C10 120.9(3) . .
C12 C11 H11 119.5 . .
C10 C11 H11 119.5 . .
C13 C12 C11 120.2(4) . .
C13 C12 H12 119.9 . .
C11 C12 H12 119.9 . .
C12 C13 C14 119.7(4) . .
C12 C13 H13 120.1 . .
C14 C13 H13 120.1 . .
C13 C14 C15 120.3(4) . .
C13 C14 H14 119.8 . .
C15 C14 H14 119.8 . .
C14 C15 C10 120.9(4) . .
C14 C15 H15 119.6 . .
C10 C15 H15 119.6 . .
O3 C16 O4 116.7(3) . .
O3 C16 C17 126.3(3) . .
O4 C16 C17 117.0(3) . .
C18 C17 C22 120.8(3) . .
C18 C17 C16 119.3(3) . .
C22 C17 C16 119.9(3) . .
C19 C18 C17 119.4(4) . .
C19 C18 H18 120.3 . .
C17 C18 H18 120.3 . .
C20 C19 C18 119.8(4) . .
C20 C19 H19 120.1 . .
C18 C19 H19 120.1 . .
C21 C20 C19 121.3(4) . .
C21 C20 H20 119.3 . .
C19 C20 H20 119.3 . .
C20 C21 C22 119.8(4) . .
C20 C21 H21 120.1 . .
C22 C21 H21 120.1 . .
C17 C22 C21 118.9(4) . .
C17 C22 C23 118.6(3) . .
C21 C22 C23 122.5(4) . .
C24 C23 C22 120.8(3) . .
C24 C23 H23 119.6 . .
C22 C23 H23 119.6 . .
C23 C24 O4 120.9(3) . .
C23 C24 C25 127.7(3) . .
O4 C24 C25 111.4(3) . .
C26 C25 C30 118.9(3) . .
C26 C25 C24 121.2(3) . .
C30 C25 C24 119.9(3) . .
C27 C26 C25 120.7(4) . .
C27 C26 H26 119.6 . .
C25 C26 H26 119.6 . .
C26 C27 C28 120.2(4) . .
C26 C27 H27 119.9 . .
C28 C27 H27 119.9 . .
C29 C28 C27 120.0(4) . .
C29 C28 H28 120.0 . .
C27 C28 H28 120.0 . .
C28 C29 C30 119.9(4) . .
C28 C29 H29 120.1 . .
C30 C29 H29 120.1 . .
C29 C30 C25 120.2(4) . .
C29 C30 H30 119.9 . .
C25 C30 H30 119.9 . .
O5 C31 O6 114.9(6) . .
O5 C31 C32 122.9(6) . .
O6 C31 C32 122.2(5) . .
C33 C32 C37 120.0(3) . .
C33 C32 C31 127.7(4) . .
C37 C32 C31 111.9(4) . .
C34 C33 C32 120.6(4) . .
C34 C33 H33 119.7 . .
C32 C33 H33 119.7 . .
C33 C34 C35 119.8(3) . .
C33 C34 H34 120.1 . .
C35 C34 H34 120.1 . .
C36 C35 C34 120.5(3) . .
C36 C35 H35 119.7 . .
C34 C35 H35 119.7 . .
C35 C36 C37 120.2(3) . .
C35 C36 H36 119.9 . .
C37 C36 H36 119.9 . .
C36 C37 C32 118.8(3) . .
C36 C37 C38 121.9(4) . .
C32 C37 C38 119.2(4) . .
O6 C38 C38 118.2(5) 2_665 2_665
O6 C38 C37 119.3(4) 2_665 .
C38 C38 C37 122.5(5) 2_665 .
C1 O2 C9 123.1(3) . .
C16 O4 C24 122.8(3) . .
C31 O5 O5 122.8(8) . 2_765
C38 O6 C31 125.8(5) 2_665 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 O1 1.216(4) .
C1 O2 1.372(4) .
C1 C2 1.455(5) .
C2 C3 1.402(5) .
C2 C7 1.405(5) .
C3 C4 1.376(5) .
C3 H3 0.9500 .
C4 C5 1.385(6) .
C4 H4 0.9500 .
C5 C6 1.382(5) .
C5 H5 0.9500 .
C6 C7 1.400(5) .
C6 H6 0.9500 .
C7 C8 1.429(5) .
C8 C9 1.337(5) .
C8 H8 0.9500 .
C9 O2 1.392(4) .
C9 C10 1.470(5) .
C10 C15 1.387(5) .
C10 C11 1.404(5) .
C11 C12 1.383(5) .
C11 H11 0.9500 .
C12 C13 1.376(5) .
C12 H12 0.9500 .
C13 C14 1.382(5) .
C13 H13 0.9500 .
C14 C15 1.386(5) .
C14 H14 0.9500 .
C15 H15 0.9500 .
C16 O3 1.210(4) .
C16 O4 1.371(4) .
C16 C17 1.461(5) .
C17 C18 1.394(5) .
C17 C22 1.399(5) .
C18 C19 1.388(6) .
C18 H18 0.9500 .
C19 C20 1.387(6) .
C19 H19 0.9500 .
C20 C21 1.375(6) .
C20 H20 0.9500 .
C21 C22 1.401(5) .
C21 H21 0.9500 .
C22 C23 1.438(5) .
C23 C24 1.332(5) .
C23 H23 0.9500 .
C24 O4 1.390(4) .
C24 C25 1.480(5) .
C25 C26 1.385(5) .
C25 C30 1.394(5) .
C26 C27 1.377(5) .
C26 H26 0.9500 .
C27 C28 1.380(6) .
C27 H27 0.9500 .
C28 C29 1.378(6) .
C28 H28 0.9500 .
C29 C30 1.392(5) .
C29 H29 0.9500 .
C30 H30 0.9500 .
C31 O5 1.207(8) .
C31 O6 1.396(8) .
C31 C32 1.433(8) .
C32 C33 1.396(5) .
C32 C37 1.398(5) .
C33 C34 1.366(5) .
C33 H33 0.9500 .
C34 C35 1.385(5) .
C34 H34 0.9500 .
C35 C36 1.385(5) .
C35 H35 0.9500 .
C36 C37 1.396(5) .
C36 H36 0.9500 .
C37 C38 1.459(5) .
C38 O6 1.191(6) 2_665
C38 C38 1.347(8) 2_665
O5 O5 1.222(10) 2_765
O6 C38 1.191(6) 2_665
