#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:32:09 +0100 (Sat 26 de Mar de 2016) $
#$Revision: 180341 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/10/7201002.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_7201002
loop_
_publ_author_name
'Saha, Pritam'
'Naskar, Subhendu'
'Paira, Priyankar'
'Hazra, Abhijit'
'Sahu, Krishnendu B.'
'Paira, Rupankar'
'Banerjee, Sukdeb'
'Mondal, Nirup B.'
_publ_section_title
;
 Basic alumina-supported highly effective Suzuki--Miyaura
 cross-coupling reaction under microwave irradiation: application to
 fused tricyclic oxa-aza-quinolones
;
_journal_issue                   7
_journal_name_full               'Green Chemistry'
_journal_page_first              931
_journal_paper_doi               10.1039/b902916h
_journal_volume                  11
_journal_year                    2009
_chemical_formula_sum            'C19 H13 N O2 S2'
_chemical_formula_weight         351.42
_chemical_name_common            oxazinoquinoline
_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                83.143(5)
_cell_angle_beta                 72.938(4)
_cell_angle_gamma                64.907(4)
_cell_formula_units_Z            2
_cell_length_a                   8.655(2)
_cell_length_b                   9.619(3)
_cell_length_c                   10.727(3)
_cell_measurement_reflns_used    7752
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.46
_cell_measurement_theta_min      1.99
_cell_volume                     773.2(4)
_computing_cell_refinement       'Kappa Apex 2'
_computing_data_collection       'Kappa Apex 2'
_computing_data_reduction        'Kappa Apex 2'
_computing_molecular_graphics    PLATON(Spek,2004)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.883
_diffrn_measured_fraction_theta_max 0.883
_diffrn_measurement_device       'Kappa Apex 2 CCD system'
_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  0.0234
_diffrn_reflns_av_sigmaI/netI    0.0309
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7752
_diffrn_reflns_theta_full        28.46
_diffrn_reflns_theta_max         28.46
_diffrn_reflns_theta_min         1.99
_diffrn_standards_decay_%        n/a
_diffrn_standards_interval_count n/a
_diffrn_standards_interval_time  n/a
_diffrn_standards_number         n/a
_exptl_absorpt_coefficient_mu    0.356
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Yellowish
_exptl_crystal_density_diffrn    1.509
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Rectangular
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.389
_refine_diff_density_min         -0.309
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     214
_refine_ls_number_reflns         3454
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      1.114
_refine_ls_R_factor_all          0.0676
_refine_ls_R_factor_gt           0.0481
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
_refine_ls_weighting_details
w=1/[σ²(Fo²)+(0.0662P)²+0.1787P] where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1288
_refine_ls_wR_factor_ref         0.1416
_reflns_number_gt                2479
_reflns_number_total             3454
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b902916h.txt
_cod_data_source_block           1
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7201002
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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 1.1110(3) 0.1830(2) 0.4480(2) 0.0480(5) Uani 1 1 d . . .
C2 C 1.1348(3) 0.2742(3) 0.3343(2) 0.0513(5) Uani 1 1 d . . .
H2 H 1.2401 0.2358 0.2685 0.062 Uiso 1 1 calc R . .
C3 C 1.00981(15) 0.41378(14) 0.31923(12) 0.0487(5) Uani 1 1 d . . .
H3 H 1.0300 0.4680 0.2429 0.058 Uiso 1 1 calc R . .
C4 C 0.71188(15) 0.62669(14) 0.40751(12) 0.0393(4) Uani 1 1 d . . .
C5 C 0.57140(15) 0.68822(14) 0.51647(12) 0.0393(4) Uani 1 1 d . . .
H5 H 0.4863 0.7870 0.5118 0.047 Uiso 1 1 calc R . .
C6 C 0.5524(2) 0.6075(2) 0.63343(18) 0.0369(4) Uani 1 1 d . . .
C7 C 0.6778(2) 0.4599(2) 0.63962(19) 0.0389(4) Uani 1 1 d . . .
C8 C 0.8256(2) 0.3967(2) 0.53305(19) 0.0387(4) Uani 1 1 d . . .
C9 C 0.8464(2) 0.4802(2) 0.41855(19) 0.0402(5) Uani 1 1 d . . .
O2 O 0.65639(19) 0.37646(15) 0.75177(14) 0.0470(4) Uani 1 1 d . . .
O1 O 1.2190(2) 0.05343(18) 0.46522(18) 0.0623(5) Uani 1 1 d . . .
N1 N 0.9544(2) 0.25005(19) 0.54358(17) 0.0431(4) Uani 1 1 d . . .
C18 C 0.7318(3) 0.2156(2) 0.7256(2) 0.0476(5) Uani 1 1 d . . .
H18A H 0.6748 0.1950 0.6689 0.057 Uiso 1 1 calc R . .
H18B H 0.7125 0.1606 0.8065 0.057 Uiso 1 1 calc R . .
C19 C 0.9250(3) 0.1620(2) 0.6622(2) 0.0490(5) Uani 1 1 d . . .
H19A H 0.9833 0.1749 0.7217 0.059 Uiso 1 1 calc R . .
H19B H 0.9751 0.0537 0.6406 0.059 Uiso 1 1 calc R . .
C11 C 0.7103(3) 0.7141(2) 0.28457(19) 0.0427(5) Uani 1 1 d . . .
C12 C 0.7425(3) 0.6512(3) 0.1644(2) 0.0564(6) Uani 1 1 d . . .
H12 H 0.7811 0.5470 0.1492 0.068 Uiso 1 1 calc R A 1
S13A S 0.7027(3) 0.7871(2) 0.0507(2) 0.0691(3) Uani 0.457(2) 1 d PD B 1
C14A C 0.6425(14) 0.9382(14) 0.1597(8) 0.0691(3) Uani 0.457(2) 1 d PD B 1
H14A H 0.6070 1.0422 0.1406 0.083 Uiso 0.457(2) 1 calc PR B 1
C13B C 0.7204(11) 0.7437(8) 0.0615(9) 0.0691(3) Uani 0.543(2) 1 d PD B 2
H13B H 0.7364 0.7162 -0.0231 0.083 Uiso 0.543(2) 1 calc PR B 2
S14B S 0.6516(3) 0.9362(3) 0.12392(13) 0.0691(3) Uani 0.543(2) 1 d PD B 2
C15 C 0.6588(3) 0.8712(3) 0.2761(2) 0.0538(6) Uani 1 1 d D . .
H15 H 0.6361 0.9290 0.3481 0.065 Uiso 1 1 calc R B 1
C41 C 0.3975(2) 0.6783(2) 0.74571(18) 0.0378(4) Uani 1 1 d . . .
C42 C 0.2327(3) 0.7842(2) 0.7305(2) 0.0467(5) Uani 1 1 d D . .
H42 H 0.2142 0.8178 0.6490 0.060(7) Uiso 1 1 calc R C 1
C43A C 0.1004(7) 0.8349(6) 0.8439(4) 0.0574(3) Uani 0.7530(19) 1 d PD D 1
H43A H -0.0160 0.9040 0.8499 0.069 Uiso 0.7530(19) 1 calc PR D 1
S44A S 0.18718(12) 0.74770(12) 0.97641(9) 0.0574(3) Uani 0.7530(19) 1 d PD D 1
S43B S 0.0869(5) 0.8394(5) 0.8701(3) 0.0574(3) Uani 0.2470(19) 1 d PD D 2
C44B C 0.2482(15) 0.7292(16) 0.9563(12) 0.0574(3) Uani 0.2470(19) 1 d PD D 2
H44B H 0.2297 0.7296 1.0461 0.069 Uiso 0.2470(19) 1 calc PR D 2
C45 C 0.3913(3) 0.6508(3) 0.8750(2) 0.0507(5) Uani 1 1 d D . .
H45 H 0.4889 0.5857 0.9043 0.061 Uiso 1 1 calc R D 1
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'
S S 0.1246 0.1234 '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
_geom_angle_publ_flag
O1 C1 N1 119.6(2) . . ?
O1 C1 C2 124.9(2) . . ?
N1 C1 C2 115.50(18) . . ?
C3 C2 C1 122.34(18) . . ?
C2 C3 C9 121.29(15) . . ?
C5 C4 C9 118.12(9) . . ?
C5 C4 C11 118.46(9) . . ?
C9 C4 C11 123.38(14) . . ?
C4 C5 C6 122.57(9) . . ?
C7 C6 C5 118.60(16) . . ?
C7 C6 C41 121.32(17) . . ?
C5 C6 C41 120.06(15) . . ?
O2 C7 C6 119.30(17) . . ?
O2 C7 C8 120.42(17) . . ?
C6 C7 C8 120.28(18) . . ?
C9 C8 N1 120.14(18) . . ?
C9 C8 C7 120.58(18) . . ?
N1 C8 C7 119.27(18) . . ?
C8 C9 C4 119.56(16) . . ?
C8 C9 C3 117.05(17) . . ?
C4 C9 C3 123.34(16) . . ?
C7 O2 C18 111.95(15) . . ?
C1 N1 C8 123.50(18) . . ?
C1 N1 C19 117.51(17) . . ?
C8 N1 C19 118.98(17) . . ?
O2 C18 C19 109.72(18) . . ?
N1 C19 C18 109.75(17) . . ?
C15 C11 C12 111.1(2) . . ?
C15 C11 C4 124.44(19) . . ?
C12 C11 C4 124.13(19) . . ?
C13B C12 C11 119.2(4) . . ?
C13B C12 S13A 8.0(4) . . ?
C11 C12 S13A 111.3(2) . . ?
C12 S13A C14A 93.7(4) . . ?
C15 C14A S13A 106.0(7) . . ?
C12 C13B S14B 104.9(6) . . ?
C15 S14B C13B 92.6(3) . . ?
C14A C15 C11 117.9(5) . . ?
C14A C15 S14B 6.0(5) . . ?
C11 C15 S14B 112.1(2) . . ?
C45 C41 C42 110.97(18) . . ?
C45 C41 C6 126.58(18) . . ?
C42 C41 C6 122.44(18) . . ?
C43A C42 C41 115.4(3) . . ?
C43A C42 S43B 4.0(4) . . ?
C41 C42 S43B 111.5(2) . . ?
C42 C43A S44A 108.7(4) . . ?
C45 S44A C43A 91.63(18) . . ?
C42 S43B C44B 91.6(5) . . ?
C45 C44B S43B 108.8(9) . . ?
C44B C45 C41 116.7(6) . . ?
C44B C45 S44A 6.6(7) . . ?
C41 C45 S44A 113.20(17) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.233(2) . ?
C1 N1 1.380(3) . ?
C1 C2 1.432(3) . ?
C2 C3 1.348(3) . ?
C3 C9 1.433(2) . ?
C4 C5 1.384(2) . ?
C4 C9 1.416(2) . ?
C4 C11 1.477(2) . ?
C5 C6 1.399(2) . ?
C6 C7 1.382(3) . ?
C6 C41 1.478(3) . ?
C7 O2 1.375(2) . ?
C7 C8 1.401(3) . ?
C8 C9 1.394(3) . ?
C8 N1 1.395(2) . ?
O2 C18 1.428(2) . ?
N1 C19 1.462(3) . ?
C18 C19 1.486(3) . ?
C11 C15 1.383(3) . ?
C11 C12 1.392(3) . ?
C12 C13B 1.338(8) . ?
C12 S13A 1.673(3) . ?
S13A C14A 1.777(10) . ?
C14A C15 1.351(9) . ?
C13B S14B 1.833(8) . ?
S14B C15 1.686(3) . ?
C41 C45 1.370(3) . ?
C41 C42 1.401(3) . ?
C42 C43A 1.371(5) . ?
C42 S43B 1.622(4) . ?
C43A S44A 1.759(5) . ?
S44A C45 1.700(2) . ?
S43B C44B 1.787(13) . ?
C44B C45 1.263(11) . ?
