#------------------------------------------------------------------------------
#$Date: 2020-03-06 02:46:29 +0200 (Fri, 06 Mar 2020) $
#$Revision: 249091 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/80/4038034.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_4038034
loop_
_publ_author_name
'Feng, Yangyang'
'Yang, Chenglin'
'Deng, Qingfu'
'Xiong, Ruimei'
'Zhang, Xiaohui'
'Xiong, Yan'
_publ_section_title
;
 Synthesis of anti Tricyclic Morpholine Derivatives through
 Iodine(III)-Mediated Intramolecular Umpolung Cycloaddition of Olefins.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c00286
_journal_year                    2020
_chemical_formula_moiety         'C17 H15 N O2'
_chemical_formula_sum            'C17 H15 N O2'
_chemical_formula_weight         265.30
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-01-22
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                104.605(3)
_cell_angle_beta                 100.400(3)
_cell_angle_gamma                103.087(3)
_cell_formula_units_Z            2
_cell_length_a                   5.7120(12)
_cell_length_b                   11.113(2)
_cell_length_c                   11.571(2)
_cell_measurement_reflns_used    1829
_cell_measurement_temperature    150
_cell_measurement_theta_max      27.355
_cell_measurement_theta_min      3.117
_cell_volume                     669.9(2)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      150.0
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.939
_diffrn_measurement_device_type  'CCD Area Detector'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0116
_diffrn_reflns_av_unetI/netI     0.0232
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.939
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            4056
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.939
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.598
_diffrn_reflns_theta_min         3.117
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6829
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0853 before and 0.0235 after correction. The Ratio of minimum to maximum transmission is 0.9159. The λ/2 correction factor is 0.00150.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_description       block
_exptl_crystal_F_000             280
_refine_diff_density_max         0.591
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2930
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0714
_refine_ls_R_factor_gt           0.0559
_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)+(0.0763P)²+0.1963P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1483
_refine_ls_wR_factor_ref         0.1614
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2232
_reflns_number_total             2930
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo0c00286_si_001.cif
_cod_data_source_block           200119fyy_0m
_cod_database_code               4038034
_shelx_shelxl_version_number     2018/3
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C4(H4), C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C11(H11), C12(H12), C13(H13), C14(H14), C15(H15), C16(H16),
 C17(H17)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_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_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 0.7094(3) 0.13885(17) -0.02015(13) 0.0726(5) Uani 1 1 d . . . . .
O2 O 0.5709(2) 0.34552(12) 0.39688(11) 0.0494(3) Uani 1 1 d . . . . .
N1 N 0.6679(3) 0.20824(14) 0.17882(13) 0.0451(4) Uani 1 1 d . . . . .
C1 C 0.7493(4) 0.13763(19) 0.08656(17) 0.0515(5) Uani 1 1 d . . . . .
C2 C 0.5279(3) 0.29747(16) 0.17424(16) 0.0435(4) Uani 1 1 d . . . . .
C3 C 0.4819(3) 0.36294(16) 0.28482(16) 0.0420(4) Uani 1 1 d . . . . .
C4 C 0.7742(4) 0.29012(19) 0.40224(16) 0.0486(4) Uani 1 1 d . . . . .
H4 H 0.924756 0.355443 0.400233 0.058 Uiso 1 1 calc R . . . .
C5 C 0.7157(4) 0.17217(18) 0.29296(16) 0.0483(4) Uani 1 1 d . . . . .
H5 H 0.563377 0.107249 0.293791 0.058 Uiso 1 1 calc R . . . .
C6 C 0.9208(4) 0.1059(2) 0.27930(17) 0.0513(5) Uani 1 1 d . . . . .
H6A H 1.086611 0.168177 0.321488 0.062 Uiso 1 1 calc R . . . .
H6B H 0.899188 0.032723 0.314385 0.062 Uiso 1 1 calc R . . . .
C7 C 0.8918(4) 0.0575(2) 0.14081(18) 0.0599(5) Uani 1 1 d . . . . .
H7A H 1.056342 0.069819 0.121990 0.072 Uiso 1 1 calc R . . . .
H7B H 0.799206 -0.035788 0.107099 0.072 Uiso 1 1 calc R . . . .
C8 C 0.8237(3) 0.26069(18) 0.52404(16) 0.0458(4) Uani 1 1 d . . . . .
C9 C 1.0616(4) 0.3024(2) 0.59683(18) 0.0574(5) Uani 1 1 d . . . . .
H9 H 1.191630 0.349290 0.570469 0.069 Uiso 1 1 calc R . . . .
C10 C 1.1151(4) 0.2771(2) 0.70825(19) 0.0659(6) Uani 1 1 d . . . . .
H10 H 1.281136 0.306615 0.757578 0.079 Uiso 1 1 calc R . . . .
C11 C 0.9292(4) 0.2095(2) 0.74811(18) 0.0595(5) Uani 1 1 d . . . . .
H11 H 0.966212 0.192370 0.824713 0.071 Uiso 1 1 calc R . . . .
C12 C 0.6894(4) 0.1671(2) 0.6759(2) 0.0609(5) Uani 1 1 d . . . . .
H12 H 0.560088 0.120575 0.702907 0.073 Uiso 1 1 calc R . . . .
C13 C 0.6352(4) 0.1919(2) 0.56335(18) 0.0561(5) Uani 1 1 d . . . . .
H13 H 0.469433 0.161905 0.513575 0.067 Uiso 1 1 calc R . . . .
C14 C 0.3381(4) 0.44799(18) 0.28597(19) 0.0517(5) Uani 1 1 d . . . . .
H14 H 0.306883 0.491014 0.361171 0.062 Uiso 1 1 calc R . . . .
C15 C 0.2401(4) 0.4703(2) 0.1777(2) 0.0636(6) Uani 1 1 d . . . . .
H15 H 0.138749 0.527344 0.178025 0.076 Uiso 1 1 calc R . . . .
C16 C 0.2899(5) 0.4094(2) 0.0691(2) 0.0697(6) Uani 1 1 d . . . . .
H16 H 0.224808 0.426232 -0.004837 0.084 Uiso 1 1 calc R . . . .
C17 C 0.4336(4) 0.3241(2) 0.06657(18) 0.0595(5) Uani 1 1 d . . . . .
H17 H 0.467849 0.283622 -0.008665 0.071 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 O2 C4 115.08(13) . . ?
C1 N1 C2 129.36(15) . . ?
C1 N1 C5 112.74(15) . . ?
C2 N1 C5 117.56(14) . . ?
O1 C1 N1 125.73(19) . . ?
O1 C1 C7 126.48(18) . . ?
N1 C1 C7 107.79(15) . . ?
C3 C2 N1 117.83(15) . . ?
C17 C2 N1 123.77(17) . . ?
C17 C2 C3 118.40(17) . . ?
O2 C3 C2 123.01(15) . . ?
O2 C3 C14 116.22(16) . . ?
C14 C3 C2 120.76(17) . . ?
O2 C4 H4 108.7 . . ?
O2 C4 C5 109.96(15) . . ?
O2 C4 C8 107.90(14) . . ?
C5 C4 H4 108.7 . . ?
C5 C4 C8 112.72(15) . . ?
C8 C4 H4 108.7 . . ?
N1 C5 C4 109.47(15) . . ?
N1 C5 H5 109.0 . . ?
N1 C5 C6 103.25(14) . . ?
C4 C5 H5 109.0 . . ?
C4 C5 C6 116.92(16) . . ?
C6 C5 H5 109.0 . . ?
C5 C6 H6A 110.8 . . ?
C5 C6 H6B 110.8 . . ?
H6A C6 H6B 108.9 . . ?
C7 C6 C5 104.57(15) . . ?
C7 C6 H6A 110.8 . . ?
C7 C6 H6B 110.8 . . ?
C1 C7 C6 105.60(16) . . ?
C1 C7 H7A 110.6 . . ?
C1 C7 H7B 110.6 . . ?
C6 C7 H7A 110.6 . . ?
C6 C7 H7B 110.6 . . ?
H7A C7 H7B 108.8 . . ?
C9 C8 C4 118.96(17) . . ?
C9 C8 C13 119.10(17) . . ?
C13 C8 C4 121.94(17) . . ?
C8 C9 H9 119.6 . . ?
C8 C9 C10 120.8(2) . . ?
C10 C9 H9 119.6 . . ?
C9 C10 H10 119.8 . . ?
C11 C10 C9 120.4(2) . . ?
C11 C10 H10 119.8 . . ?
C10 C11 H11 120.3 . . ?
C12 C11 C10 119.32(19) . . ?
C12 C11 H11 120.3 . . ?
C11 C12 H12 119.8 . . ?
C11 C12 C13 120.4(2) . . ?
C13 C12 H12 119.8 . . ?
C8 C13 C12 119.93(19) . . ?
C8 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C3 C14 H14 120.0 . . ?
C15 C14 C3 120.00(19) . . ?
C15 C14 H14 120.0 . . ?
C14 C15 H15 120.1 . . ?
C16 C15 C14 119.77(19) . . ?
C16 C15 H15 120.1 . . ?
C15 C16 H16 119.6 . . ?
C15 C16 C17 120.86(19) . . ?
C17 C16 H16 119.6 . . ?
C2 C17 H17 119.9 . . ?
C16 C17 C2 120.1(2) . . ?
C16 C17 H17 119.9 . . ?
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 C1 1.219(2) . ?
O2 C3 1.382(2) . ?
O2 C4 1.431(2) . ?
N1 C1 1.376(2) . ?
N1 C2 1.413(2) . ?
N1 C5 1.472(2) . ?
C1 C7 1.508(3) . ?
C2 C3 1.405(2) . ?
C2 C17 1.395(2) . ?
C3 C14 1.384(3) . ?
C4 H4 1.0000 . ?
C4 C5 1.497(3) . ?
C4 C8 1.518(2) . ?
C5 H5 1.0000 . ?
C5 C6 1.530(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.521(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.370(3) . ?
C8 C13 1.389(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.383(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.376(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.376(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.394(3) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C14 C15 1.383(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.380(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.386(3) . ?
C17 H17 0.9500 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C7 C6 171.8(2) . . . . ?
O2 C3 C14 C15 -179.51(17) . . . . ?
O2 C4 C5 N1 59.0(2) . . . . ?
O2 C4 C5 C6 175.93(15) . . . . ?
O2 C4 C8 C9 -130.16(18) . . . . ?
O2 C4 C8 C13 50.3(2) . . . . ?
N1 C1 C7 C6 -9.1(2) . . . . ?
N1 C2 C3 O2 1.2(3) . . . . ?
N1 C2 C3 C14 -177.56(16) . . . . ?
N1 C2 C17 C16 177.55(19) . . . . ?
N1 C5 C6 C7 -24.3(2) . . . . ?
C1 N1 C2 C3 -176.18(17) . . . . ?
C1 N1 C2 C17 3.8(3) . . . . ?
C1 N1 C5 C4 145.43(16) . . . . ?
C1 N1 C5 C6 20.2(2) . . . . ?
C2 N1 C1 O1 -1.1(3) . . . . ?
C2 N1 C1 C7 179.78(18) . . . . ?
C2 N1 C5 C4 -40.7(2) . . . . ?
C2 N1 C5 C6 -165.88(15) . . . . ?
C2 C3 C14 C15 -0.6(3) . . . . ?
C3 O2 C4 C5 -48.9(2) . . . . ?
C3 O2 C4 C8 -172.22(14) . . . . ?
C3 C2 C17 C16 -2.5(3) . . . . ?
C3 C14 C15 C16 -1.2(3) . . . . ?
C4 O2 C3 C2 19.0(2) . . . . ?
C4 O2 C3 C14 -162.18(16) . . . . ?
C4 C5 C6 C7 -144.57(18) . . . . ?
C4 C8 C9 C10 -179.69(19) . . . . ?
C4 C8 C13 C12 179.94(18) . . . . ?
C5 N1 C1 O1 171.87(19) . . . . ?
C5 N1 C1 C7 -7.2(2) . . . . ?
C5 N1 C2 C3 11.1(2) . . . . ?
C5 N1 C2 C17 -168.96(17) . . . . ?
C5 C4 C8 C9 108.2(2) . . . . ?
C5 C4 C8 C13 -71.3(2) . . . . ?
C5 C6 C7 C1 20.8(2) . . . . ?
C8 C4 C5 N1 179.48(15) . . . . ?
C8 C4 C5 C6 -63.6(2) . . . . ?
C8 C9 C10 C11 -0.1(3) . . . . ?
C9 C8 C13 C12 0.4(3) . . . . ?
C9 C10 C11 C12 0.1(3) . . . . ?
C10 C11 C12 C13 0.2(3) . . . . ?
C11 C12 C13 C8 -0.4(3) . . . . ?
C13 C8 C9 C10 -0.2(3) . . . . ?
C14 C15 C16 C17 1.2(4) . . . . ?
C15 C16 C17 C2 0.7(4) . . . . ?
C17 C2 C3 O2 -178.73(17) . . . . ?
C17 C2 C3 C14 2.5(3) . . . . ?
