#------------------------------------------------------------------------------
#$Date: 2019-11-26 14:46:14 +0200 (Tue, 26 Nov 2019) $
#$Revision: 243569 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/62/1556214.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_1556214
loop_
_publ_author_name
'Slowinski, Franck'
'Ben Ayad, Omar'
'Ziyaret, Ozge'
'Botuha, Candice'
'Le Falher, Laetitia'
'Aouane, Kamel'
'Thorimbert, Serge'
_publ_section_title
;
 Expeditive access to 2-substituted 4H-pyrido[1,3]oxazin-4-ones via an
 intramolecular O-arylation.
;
_journal_issue                   14
_journal_name_full               'Organic letters'
_journal_page_first              3494
_journal_page_last               3497
_journal_paper_doi               10.1021/ol401516e
_journal_volume                  15
_journal_year                    2013
_chemical_formula_moiety         'C13 H10 Br N2 Na O3, C4 H8 O2'
_chemical_formula_sum            'C17 H18 Br N2 Na O5'
_chemical_formula_weight         433.23
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_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   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 97.958(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.7372(8)
_cell_length_b                   18.5165(10)
_cell_length_c                   7.4853(4)
_cell_measurement_reflns_used    2407
_cell_measurement_temperature    200(1)
_cell_measurement_theta_max      22.54
_cell_measurement_theta_min      3.00
_cell_volume                     1885.66(18)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Giacovazzo et al, 1993)'
_diffrn_ambient_temperature      200(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'curved graphite'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0387
_diffrn_reflns_av_sigmaI/netI    0.0448
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            11934
_diffrn_reflns_theta_full        25.07
_diffrn_reflns_theta_max         25.07
_diffrn_reflns_theta_min         1.86
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.233
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6636
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
R.H. Blessing, Acta Cryst. (1995), A51, 33-38
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.526
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.486
_refine_diff_density_min         -0.529
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3330
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.010
_refine_ls_R_factor_all          0.0689
_refine_ls_R_factor_gt           0.0340
_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)+(0.0322P)²+0.6447P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0677
_refine_ls_wR_factor_ref         0.0779
_reflns_number_gt                2271
_reflns_number_total             3330
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            llf204.cif
_cod_data_source_block           llf204
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1556214
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
Br1 Br 0.21150(2) 0.842497(18) 0.72199(6) 0.05495(14) Uani 1 1 d .
Na1 Na 0.53800(8) 1.07588(5) 0.87596(15) 0.0324(3) Uani 1 1 d .
O1 O 0.46249(15) 0.95982(10) 0.8283(3) 0.0381(5) Uani 1 1 d .
O2 O 0.39476(15) 1.09026(10) 0.6916(3) 0.0416(6) Uani 1 1 d .
O3 O 0.69143(14) 1.06584(10) 0.7874(3) 0.0411(5) Uani 1 1 d .
H3A H 0.7386 1.0393 0.8541 0.049 Uiso 1 1 d R
H3B H 0.6804 1.0443 0.6637 0.049 Uiso 1 1 d R
O4 O 0.15969(16) 1.01550(12) -0.0175(3) 0.0516(6) Uani 1 1 d .
O5 O 0.10365(15) 1.12736(10) -0.0763(3) 0.0422(6) Uani 1 1 d .
N1 N 0.43370(18) 0.71007(12) 0.6085(3) 0.0351(6) Uani 1 1 d .
N2 N 0.33960(16) 0.97713(12) 0.5833(3) 0.0300(6) Uani 1 1 d .
C1 C 0.3345(2) 0.81134(15) 0.6632(4) 0.0290(7) Uani 1 1 d .
C2 C 0.3489(2) 0.73790(15) 0.6433(4) 0.0354(7) Uani 1 1 d .
H2 H 0.2971 0.7067 0.6548 0.042 Uiso 1 1 calc R
C3 C 0.5060(2) 0.75644(16) 0.5953(4) 0.0398(8) Uani 1 1 d .
H3C H 0.5655 0.7382 0.5691 0.048 Uiso 1 1 calc R
C4 C 0.4983(2) 0.82979(15) 0.6179(4) 0.0353(8) Uani 1 1 d .
H4 H 0.5521 0.8595 0.6100 0.042 Uiso 1 1 calc R
C5 C 0.4097(2) 0.85951(13) 0.6528(4) 0.0253(7) Uani 1 1 d .
C6 C 0.4055(2) 0.93950(14) 0.6935(4) 0.0284(7) Uani 1 1 d .
C7 C 0.3318(2) 1.05018(14) 0.6112(4) 0.0284(7) Uani 1 1 d .
C8 C 0.2365(2) 1.08359(14) 0.5276(4) 0.0289(7) Uani 1 1 d .
C9 C 0.2296(2) 1.15830(15) 0.5221(4) 0.0396(8) Uani 1 1 d .
H9 H 0.2832 1.1862 0.5699 0.048 Uiso 1 1 calc R
C10 C 0.1442(2) 1.19143(17) 0.4467(5) 0.0482(9) Uani 1 1 d .
H10 H 0.1404 1.2416 0.4434 0.058 Uiso 1 1 calc R
C11 C 0.0641(2) 1.15077(16) 0.3759(5) 0.0477(9) Uani 1 1 d .
H11 H 0.0067 1.1733 0.3235 0.057 Uiso 1 1 calc R
C12 C 0.0694(2) 1.07651(16) 0.3832(5) 0.0434(8) Uani 1 1 d .
H12 H 0.0151 1.0489 0.3374 0.052 Uiso 1 1 calc R
C13 C 0.1555(2) 1.04288(16) 0.4585(4) 0.0367(8) Uani 1 1 d .
H13 H 0.1588 0.9927 0.4627 0.044 Uiso 1 1 calc R
C14 C 0.2691(2) 1.11639(18) 0.0442(5) 0.0523(9) Uani 1 1 d .
H14A H 0.3190 1.0808 0.0784 0.078 Uiso 1 1 calc R
H14B H 0.2621 1.1465 0.1461 0.078 Uiso 1 1 calc R
H14C H 0.2875 1.1456 -0.0517 0.078 Uiso 1 1 calc R
C15 C 0.1742(2) 1.07975(18) -0.0179(4) 0.0405(8) Uani 1 1 d .
C16 C 0.0065(2) 1.09886(17) -0.1383(5) 0.0516(9) Uani 1 1 d .
H16A H -0.0156 1.0689 -0.0455 0.062 Uiso 1 1 calc R
H16B H 0.0080 1.0696 -0.2453 0.062 Uiso 1 1 calc R
C17 C -0.0612(2) 1.16141(18) -0.1800(5) 0.0563(10) Uani 1 1 d .
H17A H -0.0623 1.1899 -0.0731 0.085 Uiso 1 1 calc R
H17B H -0.1262 1.1440 -0.2218 0.085 Uiso 1 1 calc R
H17C H -0.0386 1.1906 -0.2721 0.085 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'
Na Na 0.0362 0.0249 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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
O2 Na1 O3 126.05(9) . .
O2 Na1 O1 120.10(9) . 3_677
O3 Na1 O1 112.14(9) . 3_677
O2 Na1 O1 72.02(7) . .
O3 Na1 O1 106.25(8) . .
O1 Na1 O1 80.05(8) 3_677 .
O2 Na1 N1 91.60(8) . 2_656
O3 Na1 N1 87.21(8) . 2_656
O1 Na1 N1 105.01(8) 3_677 2_656
O1 Na1 N1 162.89(9) . 2_656
O2 Na1 Na1 96.71(7) . 3_677
O3 Na1 Na1 115.32(7) . 3_677
O1 Na1 Na1 40.85(5) 3_677 3_677
O1 Na1 Na1 39.21(5) . 3_677
N1 Na1 Na1 143.21(8) 2_656 3_677
C6 O1 Na1 127.19(18) . 3_677
C6 O1 Na1 127.07(17) . .
Na1 O1 Na1 99.95(8) 3_677 .
C7 O2 Na1 136.17(18) . .
C15 O5 C16 117.2(2) . .
C3 N1 C2 116.6(2) . .
C3 N1 Na1 122.01(19) . 2_646
C2 N1 Na1 120.46(19) . 2_646
C6 N2 C7 118.7(2) . .
C5 C1 C2 120.7(3) . .
C5 C1 Br1 121.1(2) . .
C2 C1 Br1 118.0(2) . .
N1 C2 C1 122.9(3) . .
N1 C3 C4 124.0(3) . .
C3 C4 C5 119.9(3) . .
C1 C5 C4 115.9(2) . .
C1 C5 C6 125.0(2) . .
C4 C5 C6 118.8(2) . .
O1 C6 N2 129.8(3) . .
O1 C6 C5 114.9(2) . .
N2 C6 C5 115.3(2) . .
O2 C7 N2 127.1(3) . .
O2 C7 C8 117.9(2) . .
N2 C7 C8 115.0(2) . .
C13 C8 C9 118.9(3) . .
C13 C8 C7 122.7(2) . .
C9 C8 C7 118.4(3) . .
C10 C9 C8 120.6(3) . .
C9 C10 C11 120.3(3) . .
C10 C11 C12 119.7(3) . .
C11 C12 C13 120.1(3) . .
C8 C13 C12 120.3(3) . .
O4 C15 O5 122.6(3) . .
O4 C15 C14 125.9(3) . .
O5 C15 C14 111.5(3) . .
O5 C16 C17 107.7(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C1 1.893(3) .
Na1 O2 2.257(2) .
Na1 O3 2.303(2) .
Na1 O1 2.311(2) 3_677
Na1 O1 2.391(2) .
Na1 N1 2.515(3) 2_656
O1 C6 1.246(3) .
O1 Na1 2.311(2) 3_677
O2 C7 1.231(3) .
O4 C15 1.206(4) .
O5 C15 1.337(4) .
O5 C16 1.450(4) .
N1 C3 1.327(4) .
N1 C2 1.332(4) .
N1 Na1 2.515(2) 2_646
N2 C6 1.334(3) .
N2 C7 1.375(3) .
C1 C5 1.375(4) .
C1 C2 1.385(4) .
C3 C4 1.375(4) .
C4 C5 1.393(4) .
C5 C6 1.515(4) .
C7 C8 1.503(4) .
C8 C13 1.384(4) .
C8 C9 1.387(4) .
C9 C10 1.374(4) .
C10 C11 1.376(4) .
C11 C12 1.378(4) .
C12 C13 1.385(4) .
C14 C15 1.487(4) .
C16 C17 1.491(4) .
