#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:35:02 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180306 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/20/7152004.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_7152004
loop_
_publ_author_name
'Kudale, Amit A.'
'Miller, David O.'
'Dawe, Louise N.'
'Bodwell, Graham J.'
_publ_section_title
;
 Intramolecular Povarov reactions involving 3-aminocoumarins.
;
_journal_issue                   20
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              7196
_journal_page_last               7206
_journal_paper_doi               10.1039/c1ob05867c
_journal_volume                  9
_journal_year                    2011
_chemical_formula_moiety         'C25 H18 N2 O5'
_chemical_formula_sum            'C25 H18 N2 O5'
_chemical_formula_weight         426.43
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 100.732(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.814(4)
_cell_length_b                   13.493(3)
_cell_length_c                   8.7591(18)
_cell_measurement_reflns_used    7975
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      32.5311
_cell_measurement_theta_min      1.9487
_cell_volume                     1952.4(8)
_computing_cell_refinement       'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_data_collection       'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_molecular_graphics    'CrystalStructure3.7.0(Rigaku/MSC Inc.,2005)'
_computing_publication_material  'CrystalStructure3.7.0(Rigaku/MSC Inc.,2005)'
_computing_structure_refinement  'SHELXL-97 (Acta Cryst., 2008, A64, 112-122)'
_computing_structure_solution    'SHELXL-97 (Acta Cryst., 2008, A64, 112-122)'
_diffrn_ambient_temperature      153(2)
_diffrn_detector_area_resol_mean 14.63
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku Saturn'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0628
_diffrn_reflns_av_sigmaI/netI    0.0454
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            18140
_diffrn_reflns_theta_full        26.49
_diffrn_reflns_theta_max         26.49
_diffrn_reflns_theta_min         2.88
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  0.9964
_exptl_absorpt_correction_T_min  0.9784
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   '(T. Higashi, 2000)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.451
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Platelet
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.305
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     293
_refine_ls_number_reflns         4040
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.305
_refine_ls_R_factor_all          0.1154
_refine_ls_R_factor_gt           0.0992
_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)+(0.0370P)²+1.8023P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1784
_refine_ls_wR_factor_ref         0.1859
_reflns_number_gt                3488
_reflns_number_total             4040
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1ob05867c.txt
_cod_data_source_block           AAK-4-70
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Numerical' changed to
'numerical' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        1952.5(7)
_cod_database_code               7152004
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
O1 O -0.00208(13) 0.61823(17) 0.8470(3) 0.0388(6) Uani 1 1 d .
O2 O -0.00339(14) 0.58796(18) 0.5996(3) 0.0435(6) Uani 1 1 d .
O3 O 0.38353(15) 0.4039(2) 0.7007(3) 0.0563(7) Uani 1 1 d .
O4 O 0.4620(2) 0.9069(3) 1.1823(5) 0.0872(11) Uani 1 1 d .
O5 O 0.51152(19) 0.8059(3) 1.3664(4) 0.0836(11) Uani 1 1 d .
N1 N 0.14419(17) 0.5009(2) 0.6507(3) 0.0386(7) Uani 1 1 d .
N2 N 0.4649(2) 0.8257(3) 1.2463(5) 0.0633(10) Uani 1 1 d .
C1 C 0.0345(2) 0.5837(2) 0.7321(4) 0.0360(7) Uani 1 1 d .
C2 C 0.1162(2) 0.5442(2) 0.7734(4) 0.0357(7) Uani 1 1 d .
C3 C 0.21211(19) 0.4334(3) 0.6966(4) 0.0368(8) Uani 1 1 d .
H3 H 0.1943 0.3761 0.7544 0.044 Uiso 1 1 calc R
C4 C 0.2450(2) 0.3951(2) 0.5577(4) 0.0381(8) Uani 1 1 d .
C5 C 0.1950(2) 0.3698(3) 0.4186(4) 0.0424(8) Uani 1 1 d .
H5 H 0.1380 0.3747 0.4102 0.051 Uiso 1 1 calc R
C6 C 0.2266(2) 0.3375(3) 0.2913(4) 0.0454(9) Uani 1 1 d .
H6 H 0.1914 0.3200 0.1973 0.055 Uiso 1 1 calc R
C7 C 0.3092(2) 0.3313(3) 0.3024(4) 0.0493(9) Uani 1 1 d .
H7 H 0.3311 0.3110 0.2151 0.059 Uiso 1 1 calc R
C8 C 0.3602(2) 0.3546(3) 0.4407(4) 0.0518(10) Uani 1 1 d .
H8 H 0.4172 0.3494 0.4487 0.062 Uiso 1 1 calc R
C9 C 0.3281(2) 0.3855(3) 0.5678(4) 0.0443(9) Uani 1 1 d .
C10 C 0.3533(2) 0.4272(3) 0.8381(4) 0.0478(9) Uani 1 1 d .
H10A H 0.3957 0.4628 0.9114 0.057 Uiso 1 1 calc R
H10B H 0.3409 0.3650 0.8887 0.057 Uiso 1 1 calc R
C11 C 0.2776(2) 0.4908(3) 0.8043(4) 0.0387(8) Uani 1 1 d .
H11 H 0.2903 0.5520 0.7489 0.046 Uiso 1 1 calc R
C12 C 0.2485(2) 0.5225(3) 0.9541(4) 0.0385(8) Uani 1 1 d .
H12 H 0.2537 0.4641 1.0254 0.046 Uiso 1 1 calc R
C13 C 0.1600(2) 0.5532(2) 0.9193(4) 0.0359(7) Uani 1 1 d .
C14 C 0.1196(2) 0.5910(2) 1.0394(4) 0.0368(8) Uani 1 1 d .
C15 C 0.1543(2) 0.5962(3) 1.1976(4) 0.0430(9) Uani 1 1 d .
H15 H 0.2090 0.5767 1.2306 0.052 Uiso 1 1 calc R
C16 C 0.1110(2) 0.6287(3) 1.3059(4) 0.0466(9) Uani 1 1 d .
H16 H 0.1362 0.6318 1.4123 0.056 Uiso 1 1 calc R
C17 C 0.0309(2) 0.6572(3) 1.2618(4) 0.0479(9) Uani 1 1 d .
H17 H 0.0015 0.6793 1.3381 0.057 Uiso 1 1 calc R
C18 C -0.0066(2) 0.6536(3) 1.1077(4) 0.0414(8) Uani 1 1 d .
H18 H -0.0614 0.6731 1.0759 0.050 Uiso 1 1 calc R
C19 C 0.0390(2) 0.6203(3) 1.0007(4) 0.0386(8) Uani 1 1 d .
C20 C 0.3047(2) 0.6040(3) 1.0334(4) 0.0381(8) Uani 1 1 d .
C21 C 0.2938(2) 0.7018(3) 0.9851(4) 0.0424(8) Uani 1 1 d .
H21 H 0.2499 0.7185 0.9043 0.051 Uiso 1 1 calc R
C22 C 0.3462(2) 0.7758(3) 1.0531(4) 0.0475(9) Uani 1 1 d .
H22 H 0.3389 0.8428 1.0200 0.057 Uiso 1 1 calc R
C23 C 0.4092(2) 0.7485(3) 1.1703(4) 0.0478(9) Uani 1 1 d .
C24 C 0.4223(2) 0.6528(3) 1.2210(4) 0.0501(10) Uani 1 1 d .
H24 H 0.4664 0.6366 1.3018 0.060 Uiso 1 1 calc R
C25 C 0.3694(2) 0.5804(3) 1.1510(4) 0.0454(9) Uani 1 1 d .
H25 H 0.3774 0.5135 1.1840 0.055 Uiso 1 1 calc R
H1 H 0.107(2) 0.484(3) 0.571(4) 0.047 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
C1 O1 C19 120.8(3)
C9 O3 C10 117.6(3)
C2 N1 C3 114.4(3)
C2 N1 H1 116(2)
C3 N1 H1 117(2)
O5 N2 O4 123.7(4)
O5 N2 C23 119.1(4)
O4 N2 C23 117.2(4)
O2 C1 O1 117.5(3)
O2 C1 C2 123.9(3)
O1 C1 C2 118.7(3)
C13 C2 N1 124.6(3)
C13 C2 C1 121.6(3)
N1 C2 C1 113.9(3)
N1 C3 C4 112.1(3)
N1 C3 C11 107.0(3)
C4 C3 C11 109.9(3)
N1 C3 H3 109.3
C4 C3 H3 109.3
C11 C3 H3 109.3
C5 C4 C9 118.1(3)
C5 C4 C3 122.4(3)
C9 C4 C3 119.5(3)
C4 C5 C6 121.4(3)
C4 C5 H5 119.3
C6 C5 H5 119.3
C7 C6 C5 119.5(3)
C7 C6 H6 120.2
C5 C6 H6 120.2
C6 C7 C8 120.1(4)
C6 C7 H7 120.0
C8 C7 H7 120.0
C7 C8 C9 119.9(4)
C7 C8 H8 120.0
C9 C8 H8 120.0
O3 C9 C4 123.6(3)
O3 C9 C8 115.5(3)
C4 C9 C8 120.9(3)
O3 C10 C11 112.2(3)
O3 C10 H10A 109.2
C11 C10 H10A 109.2
O3 C10 H10B 109.2
C11 C10 H10B 109.2
H10A C10 H10B 107.9
C10 C11 C3 108.5(3)
C10 C11 C12 112.2(3)
C3 C11 C12 111.1(3)
C10 C11 H11 108.3
C3 C11 H11 108.3
C12 C11 H11 108.3
C13 C12 C20 113.2(3)
C13 C12 C11 111.0(3)
C20 C12 C11 108.5(3)
C13 C12 H12 108.0
C20 C12 H12 108.0
C11 C12 H12 108.0
C2 C13 C14 118.0(3)
C2 C13 C12 120.3(3)
C14 C13 C12 121.7(3)
C19 C14 C15 115.7(3)
C19 C14 C13 119.4(3)
C15 C14 C13 124.8(3)
C16 C15 C14 121.6(4)
C16 C15 H15 119.2
C14 C15 H15 119.2
C15 C16 C17 120.6(3)
C15 C16 H16 119.7
C17 C16 H16 119.7
C18 C17 C16 120.4(3)
C18 C17 H17 119.8
C16 C17 H17 119.8
C17 C18 C19 117.5(3)
C17 C18 H18 121.2
C19 C18 H18 121.2
C18 C19 C14 124.1(3)
C18 C19 O1 114.9(3)
C14 C19 O1 121.0(3)
C21 C20 C25 119.0(3)
C21 C20 C12 120.6(3)
C25 C20 C12 120.3(3)
C20 C21 C22 121.0(3)
C20 C21 H21 119.5
C22 C21 H21 119.5
C23 C22 C21 117.6(4)
C23 C22 H22 121.2
C21 C22 H22 121.2
C24 C23 C22 123.2(3)
C24 C23 N2 118.0(4)
C22 C23 N2 118.8(4)
C23 C24 C25 118.0(3)
C23 C24 H24 121.0
C25 C24 H24 121.0
C24 C25 C20 121.1(4)
C24 C25 H25 119.4
C20 C25 H25 119.4
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.356(4)
O1 C19 1.394(4)
O2 C1 1.217(4)
O3 C9 1.372(4)
O3 C10 1.426(4)
O4 N2 1.227(5)
O5 N2 1.219(5)
N1 C2 1.380(4)
N1 C3 1.458(4)
N1 H1 0.88(4)
N2 C23 1.475(5)
C1 C2 1.454(4)
C2 C13 1.357(4)
C3 C4 1.518(5)
C3 C11 1.522(4)
C3 H3 1.0000
C4 C5 1.388(4)
C4 C9 1.389(5)
C5 C6 1.392(5)
C5 H5 0.9500
C6 C7 1.376(5)
C6 H6 0.9500
C7 C8 1.384(5)
C7 H7 0.9500
C8 C9 1.389(5)
C8 H8 0.9500
C10 C11 1.518(5)
C10 H10A 0.9900
C10 H10B 0.9900
C11 C12 1.544(5)
C11 H11 1.0000
C12 C13 1.519(5)
C12 C20 1.530(5)
C12 H12 1.0000
C13 C14 1.447(4)
C14 C19 1.392(5)
C14 C15 1.402(4)
C15 C16 1.371(5)
C15 H15 0.9500
C16 C17 1.385(5)
C16 H16 0.9500
C17 C18 1.380(5)
C17 H17 0.9500
C18 C19 1.391(5)
C18 H18 0.9500
C20 C21 1.388(5)
C20 C25 1.388(4)
C21 C22 1.390(5)
C21 H21 0.9500
C22 C23 1.381(5)
C22 H22 0.9500
C23 C24 1.369(6)
C24 C25 1.386(5)
C24 H24 0.9500
C25 H25 0.9500
