#------------------------------------------------------------------------------
#$Date: 2016-03-24 00:53:47 +0100 (jue 24 de mar de 2016) $
#$Revision: 179545 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/14/4501445.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_4501445
loop_
_publ_author_name
'Aggarwal, Trapti'
'Imam, Maryam'
'Kaushik, Naveen K.'
'Chauhan, Virander S.'
'Verma, Akhilesh K.'
_publ_section_title
;
 Pyrano[4,3-b]quinolines library generation via iodocyclization and
 palladium-catalyzed coupling reactions.
;
_journal_issue                   5
_journal_name_full               'ACS combinatorial science'
_journal_page_first              530
_journal_page_last               536
_journal_paper_doi               10.1021/co200100z
_journal_volume                  13
_journal_year                    2011
_chemical_formula_sum            'C32 H24 F N O3'
_chemical_formula_weight         489.52
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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                 113.643(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.890(2)
_cell_length_b                   17.956(4)
_cell_length_c                   12.679(3)
_cell_measurement_reflns_used    5097
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.1
_cell_measurement_theta_min      3.0
_cell_volume                     2479.7(9)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.845
_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  0.0269
_diffrn_reflns_av_sigmaI/netI    0.0648
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            11395
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.07
_diffrn_reflns_theta_min         3.02
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.9842
_exptl_absorpt_correction_T_min  0.9798
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       blocks
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         1.187
_refine_diff_density_min         -0.378
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     335
_refine_ls_number_reflns         5097
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.1605
_refine_ls_R_factor_gt           0.0932
_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)+(0.0843P)²+2.9888P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2091
_refine_ls_wR_factor_ref         0.2352
_reflns_number_gt                2917
_reflns_number_total             5097
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            co200100z_si_001.cif
_cod_data_source_block           tag-167
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4501445
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 0.0919(3) 0.95624(15) 0.7758(2) 0.0494(7) Uani 1 1 d .
O2 O 0.3671(3) 0.92624(16) 0.3073(2) 0.0536(8) Uani 1 1 d .
N1 N 0.2181(3) 1.11952(17) 0.6229(3) 0.0407(8) Uani 1 1 d .
C8' C 0.1884(3) 0.9895(2) 0.6501(3) 0.0391(9) Uani 1 1 d .
F1 F 0.4642(3) 0.82094(19) -0.1085(3) 0.0974(11) Uani 1 1 d .
C7' C 0.1422(3) 0.9378(2) 0.6985(3) 0.0405(9) Uani 1 1 d .
C15' C 0.2173(4) 1.1919(2) 0.6540(3) 0.0444(10) Uani 1 1 d .
C9' C 0.1856(3) 1.0679(2) 0.6799(3) 0.0389(9) Uani 1 1 d .
C6' C 0.1316(3) 0.8563(2) 0.6763(3) 0.0422(9) Uani 1 1 d .
C20' C 0.2411(4) 0.97031(19) 0.5634(3) 0.0366(9) Uani 1 1 d .
C23' C 0.3327(4) 0.9392(2) 0.3973(3) 0.0403(9) Uani 1 1 d .
O3 O 0.2192(4) 1.01675(19) 0.9370(3) 0.0819(11) Uani 1 1 d .
C25' C 0.3513(4) 0.9349(2) 0.5922(3) 0.0438(10) Uani 1 1 d .
H8 H 0.3956 0.9207 0.6682 0.053 Uiso 1 1 calc R
C10' C 0.1498(4) 1.0857(2) 0.7713(3) 0.0445(10) Uani 1 1 d .
C22' C 0.2205(4) 0.9752(2) 0.3666(3) 0.0451(10) Uani 1 1 d .
H10 H 0.1751 0.9881 0.2902 0.054 Uiso 1 1 calc R
C24' C 0.3984(4) 0.9197(2) 0.5105(3) 0.0447(10) Uani 1 1 d .
H11 H 0.4743 0.8964 0.5323 0.054 Uiso 1 1 calc R
C26' C 0.4727(4) 0.8816(3) 0.3281(4) 0.0544(11) Uani 1 1 d .
H12A H 0.4686 0.8361 0.3677 0.065 Uiso 1 1 calc R
H12B H 0.5466 0.9084 0.3753 0.065 Uiso 1 1 calc R
C27' C 0.4736(4) 0.8639(2) 0.2128(3) 0.0442(10) Uani 1 1 d .
C14' C 0.1791(4) 1.2143(2) 0.7418(4) 0.0545(11) Uani 1 1 d .
C13' C 0.1459(4) 1.1575(2) 0.7998(4) 0.0581(12) Uani 1 1 d .
H15 H 0.1210 1.1696 0.8585 0.070 Uiso 1 1 calc R
C21' C 0.1768(4) 0.9916(2) 0.4489(3) 0.0463(10) Uani 1 1 d .
H16 H 0.1031 1.0173 0.4280 0.056 Uiso 1 1 calc R
C16' C 0.2570(5) 1.2466(2) 0.5971(4) 0.0604(12) Uani 1 1 d .
H17 H 0.2827 1.2327 0.5396 0.072 Uiso 1 1 calc R
C5' C 0.0955(4) 0.8266(2) 0.5674(4) 0.0554(11) Uani 1 1 d .
H18 H 0.0755 0.8580 0.5041 0.067 Uiso 1 1 calc R
C30' C 0.4683(5) 0.8354(3) -0.0015(4) 0.0614(13) Uani 1 1 d .
C28' C 0.5171(4) 0.9151(2) 0.1571(4) 0.0531(11) Uani 1 1 d .
H20 H 0.5478 0.9604 0.1925 0.064 Uiso 1 1 calc R
C32' C 0.4269(5) 0.7981(3) 0.1575(4) 0.0631(13) Uani 1 1 d .
H21 H 0.3971 0.7629 0.1935 0.076 Uiso 1 1 calc R
C29' C 0.5157(4) 0.9004(3) 0.0495(4) 0.0579(12) Uani 1 1 d .
H22 H 0.5469 0.9347 0.0132 0.070 Uiso 1 1 calc R
C4' C 0.0888(5) 0.7502(3) 0.5521(5) 0.0679(14) Uani 1 1 d .
H23 H 0.0647 0.7303 0.4786 0.082 Uiso 1 1 calc R
C1' C 0.1595(4) 0.8085(2) 0.7694(4) 0.0579(12) Uani 1 1 d .
H24 H 0.1823 0.8279 0.8431 0.069 Uiso 1 1 calc R
C11' C 0.1248(5) 1.0240(2) 0.8372(4) 0.0618(13) Uani 1 1 d .
H11' H 0.0547 1.0395 0.8540 0.074 Uiso 1 1 calc R
C31' C 0.4234(5) 0.7834(3) 0.0494(4) 0.0719(14) Uani 1 1 d .
H26 H 0.3910 0.7389 0.0121 0.086 Uiso 1 1 calc R
C17' C 0.2581(6) 1.3191(3) 0.6254(5) 0.0807(16) Uani 1 1 d .
H27 H 0.2854 1.3547 0.5880 0.097 Uiso 1 1 calc R
C19' C 0.1806(6) 1.2905(3) 0.7675(5) 0.0813(17) Uani 1 1 d .
H28 H 0.1552 1.3061 0.8245 0.098 Uiso 1 1 calc R
C18' C 0.2183(7) 1.3411(3) 0.7109(5) 0.096(2) Uani 1 1 d .
H29 H 0.2180 1.3913 0.7285 0.115 Uiso 1 1 calc R
C3' C 0.1177(5) 0.7036(3) 0.6451(5) 0.0731(15) Uani 1 1 d .
H30 H 0.1129 0.6523 0.6346 0.088 Uiso 1 1 calc R
C2' C 0.1536(5) 0.7329(3) 0.7537(5) 0.0740(15) Uani 1 1 d .
H31 H 0.1740 0.7013 0.8169 0.089 Uiso 1 1 calc R
C12' C 0.1933(6) 0.9712(3) 1.0201(4) 0.0927(19) Uani 1 1 d .
H32A H 0.1824 0.9203 0.9949 0.139 Uiso 1 1 calc R
H32B H 0.1199 0.9889 1.0260 0.139 Uiso 1 1 calc R
H32C H 0.2608 0.9746 1.0940 0.139 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'
F F 0.0171 0.0103 '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
C7' O1 C11' 119.7(3)
C23' O2 C26' 118.3(3)
C9' N1 C15' 118.2(3)
C7' C8' C9' 119.4(3)
C7' C8' C20' 122.7(3)
C9' C8' C20' 117.9(3)
C8' C7' O1 122.2(3)
C8' C7' C6' 127.7(3)
O1 C7' C6' 110.1(3)
N1 C15' C16' 118.4(4)
N1 C15' C14' 122.7(4)
C16' C15' C14' 118.9(4)
N1 C9' C10' 122.5(3)
N1 C9' C8' 119.4(3)
C10' C9' C8' 118.1(3)
C5' C6' C1' 118.9(4)
C5' C6' C7' 122.7(4)
C1' C6' C7' 118.4(4)
C25' C20' C21' 118.1(3)
C25' C20' C8' 123.1(3)
C21' C20' C8' 118.8(3)
C24' C23' O2 126.0(4)
C24' C23' C22' 119.3(4)
O2 C23' C22' 114.7(3)
C11' O3 C12' 113.8(4)
C20' C25' C24' 121.5(4)
C13' C10' C9' 119.2(4)
C13' C10' C11' 121.8(4)
C9' C10' C11' 119.0(4)
C21' C22' C23' 120.1(4)
C23' C24' C25' 119.9(4)
O2 C26' C27' 106.8(3)
C32' C27' C28' 118.0(4)
C32' C27' C26' 121.4(4)
C28' C27' C26' 120.6(4)
C13' C14' C19' 124.5(4)
C13' C14' C15' 116.8(4)
C19' C14' C15' 118.7(4)
C10' C13' C14' 120.6(4)
C22' C21' C20' 121.1(4)
C17' C16' C15' 120.4(4)
C6' C5' C4' 120.1(4)
C29' C30' C31' 122.5(4)
C29' C30' F1 119.0(4)
C31' C30' F1 118.5(4)
C27' C28' C29' 121.3(4)
C27' C32' C31' 121.2(4)
C30' C29' C28' 118.5(4)
C3' C4' C5' 120.2(5)
C2' C1' C6' 120.7(4)
O3 C11' O1 112.6(4)
O3 C11' C10' 109.2(4)
O1 C11' C10' 113.9(3)
C30' C31' C32' 118.6(4)
C16' C17' C18' 120.5(5)
C18' C19' C14' 120.7(5)
C19' C18' C17' 120.8(5)
C4' C3' C2' 119.9(5)
C1' C2' C3' 120.1(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C7' 1.378(4)
O1 C11' 1.413(5)
O2 C23' 1.378(4)
O2 C26' 1.422(5)
N1 C9' 1.325(4)
N1 C15' 1.359(5)
C8' C7' 1.345(5)
C8' C9' 1.463(5)
C8' C20' 1.507(5)
F1 C30' 1.363(5)
C7' C6' 1.485(5)
C15' C16' 1.408(6)
C15' C14' 1.420(5)
C9' C10' 1.422(5)
C6' C5' 1.379(5)
C6' C1' 1.388(5)
C20' C25' 1.368(5)
C20' C21' 1.396(5)
C23' C24' 1.376(5)
C23' C22' 1.390(5)
O3 C11' 1.318(5)
O3 C12' 1.460(5)
C25' C24' 1.388(5)
C10' C13' 1.345(6)
C10' C11' 1.487(6)
C22' C21' 1.372(5)
C26' C27' 1.500(5)
C27' C32' 1.371(6)
C27' C28' 1.380(6)
C14' C13' 1.404(6)
C14' C19' 1.406(6)
C16' C17' 1.348(6)
C5' C4' 1.384(6)
C30' C29' 1.343(6)
C30' C31' 1.360(7)
C28' C29' 1.384(6)
C32' C31' 1.380(6)
C4' C3' 1.372(7)
C1' C2' 1.369(6)
C17' C18' 1.403(7)
C19' C18' 1.341(7)
C3' C2' 1.372(7)
