#------------------------------------------------------------------------------
#$Date: 2016-03-26 12:46:26 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180215 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/01/7110182.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_7110182
loop_
_publ_author_name
'Sujit Mahato'
'Surajit Haldar'
'Chandan K. Jana'
_publ_section_title
;
 Diastereoselective alpha-C-H functionalization of aliphatic
 N-heterocycles: an efficient route to ring fused oxazines
;
_journal_name_full               Chem.Commun.
_journal_page_first              332
_journal_paper_doi               10.1039/c3cc46191b
_journal_volume                  50
_journal_year                    2014
_chemical_compound_source        synthesis
_chemical_formula_moiety         'C25 H21 N O'
_chemical_formula_sum            'C25 H21 N O'
_chemical_formula_weight         331.27
_chemical_name_systematic        unk
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      33
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.7114(6)
_cell_length_b                   17.5321(9)
_cell_length_c                   9.3005(4)
_cell_measurement_temperature    296(2)
_cell_volume                     1909.63(16)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0335
_diffrn_reflns_av_sigmaI/netI    0.0677
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            8121
_diffrn_reflns_theta_full        21.53
_diffrn_reflns_theta_max         21.53
_diffrn_reflns_theta_min         2.09
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.071
_exptl_crystal_density_diffrn    1.152
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             664
_exptl_crystal_recrystallization_method ethylacetate
_refine_diff_density_max         0.121
_refine_diff_density_min         -0.134
_refine_diff_density_rms         0.024
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   2(2)
_refine_ls_extinction_coef       0.0066(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.412
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         2158
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.411
_refine_ls_R_factor_all          0.0371
_refine_ls_R_factor_gt           0.0334
_refine_ls_shift/su_max          0.165
_refine_ls_shift/su_mean         0.028
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1670P)²+3.0691P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0972
_refine_ls_wR_factor_ref         0.1101
_reflns_number_gt                2015
_reflns_number_total             2158
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3cc46191b.txt
_cod_data_source_block           tst1
_cod_database_code               7110182
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, 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
C6 C 0.1806(2) 0.60885(14) 0.5494(3) 0.0514(7) Uani 1 1 d .
C4 C -0.0019(2) 0.61258(17) 0.6810(3) 0.0629(7) Uani 1 1 d .
C1 C 0.1573(2) 0.53444(15) 0.5143(3) 0.0554(7) Uani 1 1 d .
C5 C 0.1003(2) 0.64980(16) 0.6352(3) 0.0547(7) Uani 1 1 d .
C7 C 0.1190(3) 0.72530(17) 0.6813(3) 0.0679(8) Uani 1 1 d .
H7 H 0.1852 0.7506 0.6536 0.081 Uiso 1 1 calc R
C3 C -0.0204(3) 0.53645(19) 0.6409(4) 0.0710(9) Uani 1 1 d .
H3 H -0.0871 0.5121 0.6701 0.085 Uiso 1 1 calc R
C2 C 0.0561(3) 0.49787(17) 0.5610(3) 0.0684(9) Uani 1 1 d .
H2 H 0.0426 0.4472 0.5366 0.082 Uiso 1 1 calc R
C10 C -0.0811(3) 0.6534(2) 0.7659(4) 0.0839(10) Uani 1 1 d .
H10 H -0.1487 0.6298 0.7939 0.101 Uiso 1 1 calc R
C8 C 0.0408(3) 0.7618(2) 0.7663(4) 0.0871(11) Uani 1 1 d .
H8 H 0.0555 0.8113 0.7973 0.105 Uiso 1 1 calc R
C9 C -0.0604(3) 0.7262(2) 0.8071(4) 0.0946(12) Uani 1 1 d .
H9 H -0.1137 0.7523 0.8627 0.113 Uiso 1 1 calc R
C24 C 0.2903(2) 0.64594(15) 0.4987(3) 0.0542(7) Uani 1 1 d .
H24 H 0.3232 0.6728 0.5813 0.065 Uiso 1 1 calc R
C18 C 0.2744(2) 0.70444(15) 0.3793(4) 0.0590(7) Uani 1 1 d .
C12 C 0.5377(2) 0.50784(16) 0.5260(3) 0.0568(7) Uani 1 1 d .
C11 C 0.4352(2) 0.55248(18) 0.5747(3) 0.0662(8) Uani 1 1 d .
H11A H 0.3835 0.5189 0.6261 0.079 Uiso 1 1 calc R
H11B H 0.4595 0.5922 0.6405 0.079 Uiso 1 1 calc R
C13 C 0.6267(3) 0.5436(2) 0.4568(4) 0.0805(9) Uani 1 1 d .
H13 H 0.6227 0.5954 0.4359 0.097 Uiso 1 1 calc R
C17 C 0.5470(3) 0.43083(18) 0.5544(4) 0.0795(10) Uani 1 1 d .
H17 H 0.4867 0.4058 0.5994 0.095 Uiso 1 1 calc R
C19 C 0.1791(2) 0.70745(17) 0.2939(4) 0.0677(8) Uani 1 1 d .
H19 H 0.1200 0.6729 0.3090 0.081 Uiso 1 1 calc R
C23 C 0.3600(3) 0.75741(19) 0.3571(4) 0.0831(10) Uani 1 1 d .
H23 H 0.4247 0.7569 0.4151 0.100 Uiso 1 1 calc R
C20 C 0.1697(3) 0.7613(2) 0.1854(4) 0.0819(10) Uani 1 1 d .
H20 H 0.1047 0.7624 0.1280 0.098 Uiso 1 1 calc R
C22 C 0.3499(3) 0.8111(2) 0.2494(5) 0.1020(13) Uani 1 1 d .
H22 H 0.4079 0.8465 0.2357 0.122 Uiso 1 1 calc R
C21 C 0.2557(3) 0.8129(2) 0.1624(5) 0.0920(11) Uani 1 1 d .
H21 H 0.2501 0.8486 0.0888 0.110 Uiso 1 1 calc R
C15 C 0.7274(5) 0.4243(4) 0.4504(5) 0.1213(19) Uani 1 1 d .
H15 H 0.7909 0.3956 0.4244 0.146 Uiso 1 1 calc R
C14 C 0.7243(3) 0.5009(4) 0.4177(5) 0.1131(16) Uani 1 1 d .
H14 H 0.7852 0.5240 0.3708 0.136 Uiso 1 1 calc R
C16 C 0.6417(5) 0.3909(3) 0.5184(5) 0.1113(15) Uani 1 1 d .
H16 H 0.6465 0.3394 0.5417 0.134 Uiso 1 1 calc R
N1 N 0.37448(17) 0.58728(12) 0.4526(2) 0.0549(6) Uani 1 1 d .
O1 O 0.22996(16) 0.48978(10) 0.4355(2) 0.0649(5) Uani 1 1 d .
C25 C 0.3195(2) 0.53219(16) 0.3634(3) 0.0581(7) Uani 1 1 d .
H25A H 0.3764 0.4965 0.3284 0.070 Uiso 1 1 calc R
H25B H 0.2871 0.5580 0.2808 0.070 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1 C6 C5 118.7(2)
C1 C6 C24 120.2(2)
C5 C6 C24 121.1(2)
C10 C4 C3 121.9(3)
C10 C4 C5 119.1(3)
C3 C4 C5 119.0(3)
C6 C1 O1 123.2(2)
C6 C1 C2 121.6(3)
O1 C1 C2 115.2(2)
C6 C5 C7 122.8(3)
C6 C5 C4 119.3(3)
C7 C5 C4 117.9(3)
C8 C7 C5 120.8(3)
C2 C3 C4 121.5(3)
C3 C2 C1 120.0(3)
C9 C10 C4 121.2(3)
C7 C8 C9 121.1(3)
C10 C9 C8 119.9(3)
N1 C24 C6 110.8(2)
N1 C24 C18 109.7(2)
C6 C24 C18 114.4(2)
C19 C18 C23 118.6(3)
C19 C18 C24 123.2(2)
C23 C18 C24 118.3(3)
C13 C12 C17 118.4(3)
C13 C12 C11 120.6(3)
C17 C12 C11 121.0(3)
N1 C11 C12 111.6(2)
C12 C13 C14 119.4(4)
C16 C17 C12 121.5(4)
C18 C19 C20 120.8(3)
C22 C23 C18 120.3(4)
C19 C20 C21 120.3(3)
C21 C22 C23 121.0(4)
C22 C21 C20 119.0(3)
C16 C15 C14 121.1(4)
C15 C14 C13 118.8(4)
C15 C16 C17 120.8(5)
C25 N1 C11 112.7(2)
C25 N1 C24 109.7(2)
C11 N1 C24 112.6(2)
C1 O1 C25 113.80(19)
N1 C25 O1 113.9(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C6 C1 1.372(4)
C6 C5 1.427(4)
C6 C24 1.514(4)
C4 C10 1.412(4)
C4 C3 1.403(5)
C4 C5 1.429(4)
C1 O1 1.369(3)
C1 C2 1.416(4)
C5 C7 1.408(4)
C7 C8 1.369(4)
C3 C2 1.347(4)
C10 C9 1.354(5)
C8 C9 1.393(5)
C24 N1 1.488(3)
C24 C18 1.523(4)
C18 C19 1.371(4)
C18 C23 1.381(4)
C12 C13 1.376(4)
C12 C17 1.380(4)
C12 C11 1.503(4)
C11 N1 1.472(4)
C13 C14 1.413(6)
C17 C16 1.354(5)
C19 C20 1.386(5)
C23 C22 1.379(5)
C20 C21 1.371(5)
C22 C21 1.368(6)
C15 C16 1.324(7)
C15 C14 1.377(8)
N1 C25 1.427(3)
O1 C25 1.450(4)
