#------------------------------------------------------------------------------
#$Date: 2017-03-04 10:07:07 +0200 (Sat, 04 Mar 2017) $
#$Revision: 193273 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/22/4032289.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_4032289
loop_
_publ_author_name
'Bongers, Amanda'
'Clavette, Christian'
'Gan, Wei'
'Gorelsky, Serge I.'
'Betit, Lyanne'
'Lavergne, Kaitlyn'
'Markiewicz, Thomas'
'Moon, Patrick J.'
'Das Neves, Nicolas'
'Obhi, Nimrat K.'
'Toderian, Amy B.'
'Beauchemin, André M'
_publ_section_title
;
 Intermolecular Aminocarbonylation of Alkenes using Concerted
 Cycloadditions of Iminoisocyanates.
;
_journal_issue                   2
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              1175
_journal_page_last               1194
_journal_paper_doi               10.1021/acs.joc.6b02713
_journal_volume                  82
_journal_year                    2017
_chemical_formula_sum            'C14 H16 N2 O2'
_chemical_formula_weight         244.29
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 102.117(17)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.355(3)
_cell_length_b                   10.436(3)
_cell_length_c                   12.314(4)
_cell_measurement_reflns_used    6732
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      28.52
_cell_measurement_theta_min      2.23
_cell_volume                     1175.4(6)
_computing_cell_refinement       'APEX II, Bruker (2009)'
_computing_data_collection       'APEX II, Bruker (2009)'
_computing_data_reduction        'XPREP, Bruker (2009)'
_computing_molecular_graphics    'SHELXTL, Bruker (2004)'
_computing_publication_material  'SHELXTL, Bruker (2004)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.969
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0351
_diffrn_reflns_av_sigmaI/netI    0.0230
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            17491
_diffrn_reflns_theta_full        28.66
_diffrn_reflns_theta_max         28.66
_diffrn_reflns_theta_min         2.23
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.9843
_exptl_absorpt_correction_T_min  0.9743
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Bruker (2003)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.289
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2929
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0519
_refine_ls_R_factor_gt           0.0405
_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)+(0.0621P)²+0.2809P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1052
_refine_ls_wR_factor_ref         0.1148
_reflns_number_gt                2408
_reflns_number_total             2929
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo6b02713_si_004.cif
_cod_data_source_block           ab004
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/home/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

'_exptl_crystal_density_meas' value 'n/a' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               4032289
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
N1 N 0.83055(11) 0.47598(10) 0.85312(8) 0.0293(2) Uani 1 1 d .
N2 N 0.80404(10) 0.44593(9) 0.95587(7) 0.0254(2) Uani 1 1 d .
O1 O 0.84039(10) 0.36031(9) 0.69765(7) 0.0369(2) Uani 1 1 d .
O2 O 0.84561(10) 0.74086(9) 1.10698(7) 0.0341(2) Uani 1 1 d .
C1 C 0.81478(12) 0.36739(11) 0.79200(9) 0.0275(2) Uani 1 1 d .
C2 C 0.75989(12) 0.25583(11) 0.85162(9) 0.0256(2) Uani 1 1 d .
H2A H 0.8261 0.1798 0.8579 0.031 Uiso 1 1 calc R
C3 C 0.59912(13) 0.22100(12) 0.80016(9) 0.0305(3) Uani 1 1 d .
H3A H 0.5767 0.2112 0.7175 0.037 Uiso 1 1 calc R
C4 C 0.55463(14) 0.10649(13) 0.86375(11) 0.0358(3) Uani 1 1 d .
H4A H 0.6273 0.0364 0.8701 0.043 Uiso 1 1 calc R
H4B H 0.4574 0.0733 0.8268 0.043 Uiso 1 1 calc R
C5 C 0.55072(14) 0.16390(13) 0.97967(10) 0.0342(3) Uani 1 1 d .
H5A H 0.4529 0.1537 0.9973 0.041 Uiso 1 1 calc R
H5B H 0.6246 0.1228 1.0388 0.041 Uiso 1 1 calc R
C6 C 0.58673(12) 0.30579(12) 0.96639(9) 0.0293(3) Uani 1 1 d .
H6A H 0.5543 0.3653 1.0202 0.035 Uiso 1 1 calc R
C7 C 0.75159(12) 0.31129(11) 0.96515(9) 0.0254(2) Uani 1 1 d .
H7A H 0.8132 0.2630 1.0282 0.030 Uiso 1 1 calc R
C8 C 0.51627(13) 0.32937(13) 0.84365(10) 0.0336(3) Uani 1 1 d .
H8A H 0.4091 0.3159 0.8270 0.040 Uiso 1 1 calc R
H8B H 0.5399 0.4149 0.8173 0.040 Uiso 1 1 calc R
C9 C 0.81906(12) 0.52973(12) 1.03665(9) 0.0269(2) Uani 1 1 d .
C10 C 0.84489(12) 0.66213(12) 1.01651(9) 0.0289(3) Uani 1 1 d .
C11 C 0.86521(14) 0.73507(12) 0.92836(11) 0.0341(3) Uani 1 1 d .
H11A H 0.8692 0.7053 0.8562 0.041 Uiso 1 1 calc R
C12 C 0.87899(14) 0.86349(13) 0.96605(12) 0.0386(3) Uani 1 1 d .
H12A H 0.8949 0.9365 0.9241 0.046 Uiso 1 1 calc R
C13 C 0.86517(13) 0.86237(13) 1.07330(12) 0.0380(3) Uani 1 1 d .
H13A H 0.8687 0.9363 1.1187 0.046 Uiso 1 1 calc R
C14 C 0.81189(14) 0.48678(13) 1.15187(9) 0.0328(3) Uani 1 1 d .
H14A H 0.8348 0.3952 1.1598 0.049 Uiso 1 1 calc R
H14B H 0.7133 0.5018 1.1646 0.049 Uiso 1 1 calc R
H14C H 0.8829 0.5353 1.2063 0.049 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 N1 N2 107.54(9)
C9 N2 N1 122.34(10)
C9 N2 C7 123.51(9)
N1 N2 C7 114.12(9)
C13 O2 C10 106.67(10)
O1 C1 N1 123.59(11)
O1 C1 C2 123.98(11)
N1 C1 C2 112.42(10)
C1 C2 C7 103.79(9)
C1 C2 C3 112.30(9)
C7 C2 C3 103.39(9)
C8 C3 C4 100.70(10)
C8 C3 C2 101.73(9)
C4 C3 C2 108.58(10)
C3 C4 C5 103.27(10)
C6 C5 C4 103.05(10)
C5 C6 C8 101.59(10)
C5 C6 C7 106.17(10)
C8 C6 C7 101.95(9)
N2 C7 C2 101.80(9)
N2 C7 C6 112.22(9)
C2 C7 C6 103.71(9)
C3 C8 C6 94.68(9)
N2 C9 C10 120.50(10)
N2 C9 C14 119.93(11)
C10 C9 C14 119.56(10)
C11 C10 O2 109.25(11)
C11 C10 C9 136.76(11)
O2 C10 C9 113.95(10)
C10 C11 C12 106.52(12)
C13 C12 C11 106.91(12)
C12 C13 O2 110.64(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C1 1.3513(16)
N1 N2 1.3756(13)
N2 C9 1.3097(15)
N2 C7 1.5006(15)
O1 C1 1.2367(15)
O2 C13 1.3584(17)
O2 C10 1.3831(14)
C1 C2 1.5219(16)
C2 C7 1.5300(16)
C2 C3 1.5478(16)
C3 C8 1.5300(18)
C3 C4 1.5334(18)
C4 C5 1.5556(18)
C5 C6 1.5349(18)
C6 C8 1.5366(17)
C6 C7 1.5466(16)
C9 C10 1.4333(18)
C9 C14 1.5027(16)
C10 C11 1.3713(18)
C11 C12 1.4153(19)
C12 C13 1.354(2)
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
C1 N1 N2 C9 175.95(10)
C1 N1 N2 C7 -6.19(12)
N2 N1 C1 O1 -175.25(10)
N2 N1 C1 C2 5.63(12)
O1 C1 C2 C7 177.82(10)
N1 C1 C2 C7 -3.06(12)
O1 C1 C2 C3 -71.18(15)
N1 C1 C2 C3 107.93(11)
C1 C2 C3 C8 -75.50(12)
C7 C2 C3 C8 35.75(11)
C1 C2 C3 C4 178.85(10)
C7 C2 C3 C4 -69.90(12)
C8 C3 C4 C5 -37.41(11)
C2 C3 C4 C5 68.96(12)
C3 C4 C5 C6 2.47(12)
C4 C5 C6 C8 33.21(12)
C4 C5 C6 C7 -73.02(11)
C9 N2 C7 C2 -178.07(10)
N1 N2 C7 C2 4.10(11)
C9 N2 C7 C6 71.63(13)
N1 N2 C7 C6 -106.20(10)
C1 C2 C7 N2 -0.58(10)
C3 C2 C7 N2 -117.97(9)
C1 C2 C7 C6 116.08(10)
C3 C2 C7 C6 -1.31(11)
C5 C6 C7 N2 -178.33(8)
C8 C6 C7 N2 75.70(11)
C5 C6 C7 C2 72.59(10)
C8 C6 C7 C2 -33.38(11)
C4 C3 C8 C6 56.83(10)
C2 C3 C8 C6 -54.91(11)
C5 C6 C8 C3 -55.45(11)
C7 C6 C8 C3 54.05(11)
N1 N2 C9 C10 8.58(16)
C7 N2 C9 C10 -169.08(10)
N1 N2 C9 C14 -170.34(10)
C7 N2 C9 C14 12.01(16)
C13 O2 C10 C11 0.53(13)
C13 O2 C10 C9 -177.55(10)
N2 C9 C10 C11 -2.7(2)
C14 C9 C10 C11 176.18(13)
N2 C9 C10 O2 174.61(9)
C14 C9 C10 O2 -6.47(15)
O2 C10 C11 C12 0.02(13)
C9 C10 C11 C12 177.46(13)
C10 C11 C12 C13 -0.57(14)
C11 C12 C13 O2 0.93(14)
C10 O2 C13 C12 -0.91(13)
