#------------------------------------------------------------------------------
#$Date: 2016-03-26 12:46:26 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180215 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/01/7110187.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_7110187
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         'C21 H21 N O'
_chemical_formula_sum            'C21 H21 N O'
_chemical_formula_weight         303.39
_chemical_name_systematic
rac-(1R,3S)-2-ethyl-3-methyl-1-phenyl-2,3-dihydro-1H-naphtho[1,2-e][1,3]oxazine
_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                 94.061(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.4433(3)
_cell_length_b                   11.6711(4)
_cell_length_c                   17.1926(6)
_cell_measurement_temperature    296(2)
_cell_volume                     1689.95(10)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1741
_diffrn_reflns_av_sigmaI/netI    0.1151
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            19899
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.11
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.192
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             648
_exptl_crystal_recrystallization_method ethylacetate
_refine_diff_density_max         0.125
_refine_diff_density_min         -0.148
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.890
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         2964
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.890
_refine_ls_R_factor_all          0.1216
_refine_ls_R_factor_gt           0.0479
_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)+(0.0000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0644
_refine_ls_wR_factor_ref         0.0732
_reflns_number_gt                1258
_reflns_number_total             2964
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3cc46191b.txt
_cod_data_source_block           shhhhh
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7110187
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
C7 C 0.2753(3) 0.14081(18) 0.32052(13) 0.0448(7) Uani 1 1 d .
C1 C 0.1413(3) 0.3245(2) 0.34228(16) 0.0553(7) Uani 1 1 d .
C8 C 0.2183(3) 0.1457(2) 0.24372(15) 0.0542(7) Uani 1 1 d .
C6 C 0.2360(3) 0.23179(19) 0.37109(14) 0.0479(7) Uani 1 1 d .
C5 C 0.2925(3) 0.23491(18) 0.45033(13) 0.0562(7) Uani 1 1 d .
H5 H 0.3522 0.1739 0.4712 0.067 Uiso 1 1 calc R
C2 C 0.1114(3) 0.4171(2) 0.39205(17) 0.0732(9) Uani 1 1 d .
H2 H 0.0503 0.4785 0.3728 0.088 Uiso 1 1 calc R
C9 C 0.1216(3) 0.2363(2) 0.21457(13) 0.0696(8) Uani 1 1 d .
H9 H 0.0839 0.2371 0.1624 0.083 Uiso 1 1 calc R
C4 C 0.2612(3) 0.3259(2) 0.49690(13) 0.0686(8) Uani 1 1 d .
H4 H 0.3008 0.3265 0.5488 0.082 Uiso 1 1 calc R
C10 C 0.0834(3) 0.32293(19) 0.26303(17) 0.0696(8) Uani 1 1 d .
H10 H 0.0181 0.3820 0.2436 0.084 Uiso 1 1 calc R
C3 C 0.1703(4) 0.4177(2) 0.46724(17) 0.0784(10) Uani 1 1 d .
H3 H 0.1501 0.4795 0.4992 0.094 Uiso 1 1 calc R
O1 O 0.2562(2) 0.06631(14) 0.18857(7) 0.0686(5) Uani 1 1 d .
C17 C 0.3858(3) 0.04398(17) 0.34629(11) 0.0476(6) Uani 1 1 d .
H17 H 0.4677 0.0766 0.3830 0.057 Uiso 1 1 calc R
C12 C 0.3075(3) -0.0533(2) 0.38873(11) 0.0491(7) Uani 1 1 d .
C11 C 0.1569(3) -0.04400(19) 0.41404(12) 0.0586(8) Uani 1 1 d .
H11 H 0.0990 0.0228 0.4038 0.070 Uiso 1 1 calc R
C14 C 0.3211(4) -0.2440(2) 0.44273(14) 0.0840(10) Uani 1 1 d .
H14 H 0.3772 -0.3119 0.4517 0.101 Uiso 1 1 calc R
C15 C 0.1716(4) -0.2320(2) 0.46866(14) 0.0761(9) Uani 1 1 d .
H15 H 0.1265 -0.2914 0.4956 0.091 Uiso 1 1 calc R
C13 C 0.3879(3) -0.1548(2) 0.40311(12) 0.0705(8) Uani 1 1 d .
H13 H 0.4892 -0.1635 0.3859 0.085 Uiso 1 1 calc R
C16 C 0.0900(3) -0.1324(2) 0.45457(12) 0.0684(8) Uani 1 1 d .
H16 H -0.0109 -0.1237 0.4722 0.082 Uiso 1 1 calc R
N2 N 0.4680(3) -0.00195(14) 0.27966(10) 0.0531(6) Uani 1 1 d .
C18 C 0.3496(3) -0.03177(18) 0.21941(14) 0.0599(7) Uani 1 1 d .
H18 H 0.2758 -0.0850 0.2421 0.072 Uiso 1 1 calc R
C19 C 0.5945(3) 0.0748(2) 0.25489(13) 0.0735(8) Uani 1 1 d .
H19A H 0.5506 0.1507 0.2452 0.088 Uiso 1 1 calc R
H19B H 0.6321 0.0466 0.2064 0.088 Uiso 1 1 calc R
C20 C 0.7337(3) 0.08318(19) 0.31554(14) 0.1010(10) Uani 1 1 d .
H20A H 0.7027 0.1262 0.3595 0.151 Uiso 1 1 calc R
H20B H 0.8208 0.1210 0.2933 0.151 Uiso 1 1 calc R
H20C H 0.7657 0.0076 0.3322 0.151 Uiso 1 1 calc R
C21 C 0.4100(3) -0.08985(16) 0.14806(11) 0.0851(9) Uani 1 1 d .
H21A H 0.4628 -0.0345 0.1177 0.128 Uiso 1 1 calc R
H21B H 0.3221 -0.1222 0.1170 0.128 Uiso 1 1 calc R
H21C H 0.4832 -0.1495 0.1644 0.128 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'
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'
H H 0.0000 0.0000 '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
C8 C7 C6 118.3(2)
C8 C7 C17 118.6(2)
C6 C7 C17 122.9(2)
C2 C1 C6 119.6(3)
C2 C1 C10 122.0(3)
C6 C1 C10 118.4(2)
C7 C8 O1 123.4(2)
C7 C8 C9 121.9(2)
O1 C8 C9 114.6(2)
C5 C6 C1 117.5(2)
C5 C6 C7 122.0(2)
C1 C6 C7 120.4(2)
C4 C5 C6 121.3(2)
C3 C2 C1 121.0(3)
C10 C9 C8 119.8(2)
C5 C4 C3 120.5(2)
C9 C10 C1 121.2(2)
C2 C3 C4 120.1(3)
C8 O1 C18 114.85(17)
N2 C17 C7 110.94(17)
N2 C17 C12 110.07(17)
C7 C17 C12 114.6(2)
C11 C12 C13 117.7(2)
C11 C12 C17 122.2(2)
C13 C12 C17 120.0(2)
C12 C11 C16 121.2(2)
C15 C14 C13 119.8(3)
C16 C15 C14 119.5(3)
C12 C13 C14 121.4(3)
C15 C16 C11 120.3(3)
C18 N2 C19 114.88(18)
C18 N2 C17 107.8(2)
C19 N2 C17 112.99(17)
N2 C18 O1 113.71(17)
N2 C18 C21 115.8(2)
O1 C18 C21 104.99(19)
N2 C19 C20 112.4(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C7 C8 1.374(2)
C7 C6 1.426(2)
C7 C17 1.512(2)
C1 C2 1.412(3)
C1 C6 1.414(3)
C1 C10 1.415(3)
C8 O1 1.379(2)
C8 C9 1.406(3)
C6 C5 1.412(2)
C5 C4 1.367(2)
C2 C3 1.352(3)
C9 C10 1.363(2)
C4 C3 1.393(3)
O1 C18 1.468(2)
C17 N2 1.481(2)
C17 C12 1.526(2)
C12 C11 1.377(3)
C12 C13 1.378(3)
C11 C16 1.387(2)
C14 C15 1.375(3)
C14 C13 1.386(3)
C15 C16 1.364(3)
N2 C18 1.431(3)
N2 C19 1.480(2)
C18 C21 1.521(2)
C19 C20 1.518(3)
