#------------------------------------------------------------------------------
#$Date: 2020-05-07 19:54:20 +0300 (Thu, 07 May 2020) $
#$Revision: 251866 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/83/4038334.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_4038334
loop_
_publ_author_name
'Kumar, Pankaj'
'Kumar, Rakesh'
'Banerjee, Prabal'
_publ_section_title
;
 Accessing Dihydro-1,2-oxazine via Cloke-Wilson type Annulation of
 Cyclopropyl Carbonyls: Application towards the Diastereoselective
 Synthesis of Pyrrolo[1,2-b][1,2]oxazine.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c00531
_journal_year                    2020
_chemical_formula_moiety         'C17 H17 N O2'
_chemical_formula_sum            'C17 H17 N O2'
_chemical_formula_weight         267.31
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 92.464(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   62.025(4)
_cell_length_b                   5.3766(3)
_cell_length_c                   8.2455(5)
_cell_measurement_reflns_used    12191
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      28.3
_cell_measurement_theta_min      2.6
_cell_volume                     2747.2(3)
_computing_cell_refinement       'APEX2 (Bruker, 2014); SAINT (Bruker, 2014)'
_computing_data_collection       'APEX2 (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014);XPREP(Sheldrick,2014)'
_computing_molecular_graphics    'Ortep, Platon, mercury'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean 10.233
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.947
_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON 100 CMOS'
_diffrn_measurement_method       'phi and omega scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0227
_diffrn_reflns_av_unetI/netI     0.0244
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.947
_diffrn_reflns_limit_h_max       82
_diffrn_reflns_limit_h_min       -81
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            12191
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.947
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.269
_diffrn_reflns_theta_min         2.630
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6519
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_density_meas      1.29
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1136
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.340
_exptl_crystal_size_min          0.250
_exptl_transmission_factor_max   0.7457
_exptl_transmission_factor_min   0.6504
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.165
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         3219
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0757
_refine_ls_R_factor_gt           0.0576
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0367P)²+2.8841P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1225
_refine_ls_wR_factor_ref         0.1326
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2554
_reflns_number_total             3219
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo0c00531_si_002.cif
_cod_data_source_block           shelx
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4038334
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.970
_shelx_estimated_absorpt_t_max   0.979
loop_
_space_group_symop_operation_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'
'-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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.05380(2) 0.3972(2) -0.00313(15) 0.0459(3) Uani 1 1 d . . . . .
O2 O 0.15252(2) 0.2684(3) 0.00386(16) 0.0546(4) Uani 1 1 d . . . . .
N1 N 0.03117(2) 0.4327(3) -0.0005(2) 0.0531(4) Uani 1 1 d . . . . .
C12 C 0.08723(3) 0.2471(3) 0.10007(19) 0.0365(4) Uani 1 1 d . . . . .
C13 C 0.10101(3) 0.4305(3) 0.1621(2) 0.0460(4) Uani 1 1 d . . . . .
H13 H 0.0956 0.5552 0.2271 0.055 Uiso 1 1 calc R U . . .
C16 C 0.05209(3) 0.0142(3) 0.1497(2) 0.0428(4) Uani 1 1 d . . . . .
H16A H 0.0588 -0.0823 0.2377 0.051 Uiso 1 1 calc R U . . .
H16B H 0.0528 -0.0809 0.0501 0.051 Uiso 1 1 calc R U . . .
C11 C 0.09592(3) 0.0626(3) 0.0060(2) 0.0427(4) Uani 1 1 d . . . . .
H11 H 0.0870 -0.0638 -0.0348 0.051 Uiso 1 1 calc R U . . .
C8 C 0.16176(3) 0.0901(4) -0.1012(2) 0.0512(5) Uani 1 1 d . . . . .
H8A H 0.1535 0.0829 -0.2036 0.061 Uiso 1 1 calc R U . . .
H8B H 0.1617 -0.0736 -0.0518 0.061 Uiso 1 1 calc R U . . .
C1 C 0.02075(3) 0.2861(4) 0.0869(2) 0.0501(5) Uani 1 1 d . . . . .
H1 H 0.0060 0.3179 0.0905 0.060 Uiso 1 1 calc R U . . .
C15 C 0.06358(3) 0.2587(3) 0.13347(19) 0.0372(4) Uani 1 1 d . . . . .
H15 H 0.0618 0.3552 0.2329 0.045 Uiso 1 1 calc R U . . .
C14 C 0.12256(3) 0.4307(4) 0.1291(2) 0.0487(5) Uani 1 1 d . . . . .
H14 H 0.1316 0.5545 0.1724 0.058 Uiso 1 1 calc R U . . .
C2 C 0.18452(3) 0.1691(4) -0.1289(2) 0.0443(4) Uani 1 1 d . . . . .
C9 C 0.13094(3) 0.2475(3) 0.0317(2) 0.0400(4) Uani 1 1 d . . . . .
C10 C 0.11759(3) 0.0609(3) -0.0293(2) 0.0438(4) Uani 1 1 d . . . . .
H10 H 0.1231 -0.0646 -0.0933 0.053 Uiso 1 1 calc R U . . .
C17 C 0.02871(3) 0.0704(4) 0.1845(2) 0.0481(4) Uani 1 1 d . . . . .
H17A H 0.0199 -0.0741 0.1586 0.058 Uiso 1 1 calc R U . . .
H17B H 0.0276 0.1066 0.2991 0.058 Uiso 1 1 calc R U . . .
C3 C 0.20168(3) 0.0294(4) -0.0685(3) 0.0558(5) Uani 1 1 d . . . . .
H3 H 0.1991 -0.1123 -0.0076 0.067 Uiso 1 1 calc R U . . .
C5 C 0.22650(4) 0.3071(5) -0.1859(3) 0.0697(7) Uani 1 1 d . . . . .
H5 H 0.2406 0.3535 -0.2053 0.084 Uiso 1 1 calc R U . . .
C4 C 0.22265(3) 0.0980(5) -0.0975(3) 0.0676(6) Uani 1 1 d . . . . .
H4 H 0.2341 0.0019 -0.0569 0.081 Uiso 1 1 calc R U . . .
C6 C 0.20966(4) 0.4479(5) -0.2458(3) 0.0693(6) Uani 1 1 d . . . . .
H6 H 0.2123 0.5904 -0.3057 0.083 Uiso 1 1 calc R U . . .
C7 C 0.18868(3) 0.3797(4) -0.2178(3) 0.0580(5) Uani 1 1 d . . . . .
H7 H 0.1773 0.4763 -0.2592 0.070 Uiso 1 1 calc R U . . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 O1 C15 115.83(12) . . ?
C9 O2 C8 117.78(14) . . ?
C1 N1 O1 117.11(15) . . ?
C11 C12 C13 117.86(15) . . ?
C11 C12 C15 122.61(15) . . ?
C13 C12 C15 119.52(15) . . ?
C14 C13 C12 121.07(16) . . ?
C15 C16 C17 107.61(15) . . ?
C12 C11 C10 121.80(16) . . ?
O2 C8 C2 107.89(15) . . ?
N1 C1 C17 129.03(17) . . ?
O1 C15 C16 109.36(13) . . ?
O1 C15 C12 104.82(12) . . ?
C16 C15 C12 116.70(14) . . ?
C13 C14 C9 120.39(17) . . ?
C3 C2 C7 118.72(18) . . ?
C3 C2 C8 120.50(18) . . ?
C7 C2 C8 120.77(18) . . ?
O2 C9 C10 124.93(16) . . ?
O2 C9 C14 115.55(15) . . ?
C10 C9 C14 119.52(16) . . ?
C9 C10 C11 119.34(16) . . ?
C1 C17 C16 110.54(15) . . ?
C2 C3 C4 120.7(2) . . ?
C6 C5 C4 120.0(2) . . ?
C5 C4 C3 119.9(2) . . ?
C5 C6 C7 120.3(2) . . ?
C2 C7 C6 120.4(2) . . ?
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
O1 N1 1.4178(18) . ?
O1 C15 1.4603(19) . ?
O2 C9 1.3718(19) . ?
O2 C8 1.428(2) . ?
N1 C1 1.265(2) . ?
C12 C11 1.383(2) . ?
C12 C13 1.388(2) . ?
C12 C15 1.505(2) . ?
C13 C14 1.376(2) . ?
C16 C15 1.504(2) . ?
C16 C17 1.520(2) . ?
C11 C10 1.387(2) . ?
C8 C2 1.501(2) . ?
C1 C17 1.484(3) . ?
C14 C9 1.386(2) . ?
C2 C3 1.378(3) . ?
C2 C7 1.379(3) . ?
C9 C10 1.382(2) . ?
C3 C4 1.383(3) . ?
C5 C6 1.365(3) . ?
C5 C4 1.367(3) . ?
C6 C7 1.381(3) . ?
