#------------------------------------------------------------------------------
#$Date: 2019-11-24 19:01:57 +0200 (Sun, 24 Nov 2019) $
#$Revision: 239107 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/57/1555777.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_1555777
loop_
_publ_author_name
'Gao, Mingchun'
'Xu, Bin'
_publ_section_title
;
 Copper Nitrate Mediated Regio- and Stereoselective Difunctionalization of
 Alkynes: A Direct Approach to α-Chloro-β-nitroolefins.
;
_journal_issue                   18
_journal_name_full               'Organic letters'
_journal_page_first              4746
_journal_page_last               4749
_journal_paper_doi               10.1021/acs.orglett.6b02464
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C14 H18 N2 O2'
_chemical_formula_sum            'C14 H18 N2 O2'
_chemical_formula_weight         246.30
_chemical_name_common            (E)-1-(2-Nitro-1-(p-tolyl)vinyl)piperidine
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_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                 94.878(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.018(6)
_cell_length_b                   16.118(13)
_cell_length_c                   10.272(8)
_cell_measurement_reflns_used    2215
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.42
_cell_measurement_theta_min      2.5
_cell_volume                     1322.7(18)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.0
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker AMART 1000'
_diffrn_measurement_method       ω
_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  0.0246
_diffrn_reflns_av_sigmaI/netI    0.0285
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8060
_diffrn_reflns_theta_full        27.42
_diffrn_reflns_theta_max         27.42
_diffrn_reflns_theta_min         2.36
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_correction_T_min  0.981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Higashi, 1995)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.237
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.218
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       0.029(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     168
_refine_ls_number_reflns         2984
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0585
_refine_ls_R_factor_gt           0.0439
_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)+(0.0603P)²+0.2262P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1189
_refine_ls_wR_factor_ref         0.1290
_reflns_number_gt                2243
_reflns_number_total             2984
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol6b02464_si_003.cif
_cod_data_source_block           compound_4
_cod_original_cell_volume        1322.6(18)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1555777
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
O1 O 0.27786(13) 0.17336(7) 0.84126(12) 0.0531(3) Uani 1 1 d .
N2 N 0.78246(14) 0.20157(7) 0.95592(12) 0.0389(3) Uani 1 1 d .
O2 O 0.29189(15) 0.05122(8) 0.92753(18) 0.0800(5) Uani 1 1 d .
N1 N 0.35853(15) 0.11836(8) 0.90185(13) 0.0441(3) Uani 1 1 d .
C8 C 0.61424(17) 0.20096(8) 0.94108(13) 0.0333(3) Uani 1 1 d .
C5 C 0.53937(19) 0.33360(10) 0.81979(14) 0.0415(4) Uani 1 1 d .
H5 H 0.6076 0.3177 0.7553 0.050 Uiso 1 1 calc R
C10 C 0.88272(19) 0.27498(9) 0.99565(15) 0.0430(4) Uani 1 1 d .
H10A H 0.8131 0.3242 0.9866 0.052 Uiso 1 1 calc R
H10B H 0.9730 0.2812 0.9392 0.052 Uiso 1 1 calc R
C9 C 0.52802(18) 0.12724(9) 0.94329(15) 0.0406(4) Uani 1 1 d .
C3 C 0.42773(19) 0.30913(9) 1.02419(15) 0.0410(4) Uani 1 1 d .
H3 H 0.4192 0.2765 1.0980 0.049 Uiso 1 1 calc R
C14 C 0.88370(18) 0.12523(10) 0.96630(16) 0.0446(4) Uani 1 1 d .
H14A H 0.9751 0.1296 0.9106 0.053 Uiso 1 1 calc R
H14B H 0.8150 0.0782 0.9370 0.053 Uiso 1 1 calc R
C4 C 0.52628(17) 0.28285(8) 0.92726(13) 0.0341(3) Uani 1 1 d .
C11 C 0.9549(2) 0.26631(10) 1.13666(15) 0.0473(4) Uani 1 1 d .
H11A H 0.8646 0.2661 1.1938 0.057 Uiso 1 1 calc R
H11B H 1.0266 0.3134 1.1600 0.057 Uiso 1 1 calc R
C1 C 0.3512(2) 0.43351(10) 0.90216(16) 0.0471(4) Uani 1 1 d .
C6 C 0.4526(2) 0.40749(10) 0.80708(16) 0.0481(4) Uani 1 1 d .
H6 H 0.4623 0.4404 0.7337 0.058 Uiso 1 1 calc R
C12 C 1.0556(2) 0.18655(11) 1.15610(17) 0.0528(4) Uani 1 1 d .
H12A H 1.1557 0.1905 1.1097 0.063 Uiso 1 1 calc R
H12B H 1.0899 0.1794 1.2483 0.063 Uiso 1 1 calc R
C13 C 0.9533(2) 0.11165(11) 1.10657(16) 0.0518(4) Uani 1 1 d .
H13A H 1.0235 0.0625 1.1118 0.062 Uiso 1 1 calc R
H13B H 0.8619 0.1028 1.1611 0.062 Uiso 1 1 calc R
C2 C 0.3420(2) 0.38382(10) 1.01127(16) 0.0473(4) Uani 1 1 d .
H2 H 0.2771 0.4009 1.0772 0.057 Uiso 1 1 calc R
C7 C 0.2529(3) 0.51334(12) 0.8878(2) 0.0733(6) Uani 1 1 d .
H7A H 0.2741 0.5398 0.8071 0.110 Uiso 1 1 calc R
H7B H 0.2865 0.5496 0.9595 0.110 Uiso 1 1 calc R
H7C H 0.1356 0.5014 0.8877 0.110 Uiso 1 1 calc R
H9 H 0.574(2) 0.0768(10) 0.9753(15) 0.044(4) Uiso 1 1 d .
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
C8 N2 C10 123.89(12)
C8 N2 C14 122.92(12)
C10 N2 C14 111.57(13)
O1 N1 O2 121.01(14)
O1 N1 C9 122.33(13)
O2 N1 C9 116.65(13)
N2 C8 C9 120.33(13)
N2 C8 C4 117.65(12)
C9 C8 C4 121.97(13)
C6 C5 C4 120.89(15)
N2 C10 C11 110.24(12)
C8 C9 N1 124.11(14)
C2 C3 C4 120.24(14)
N2 C14 C13 110.21(12)
C5 C4 C3 118.53(14)
C5 C4 C8 121.94(13)
C3 C4 C8 119.53(13)
C10 C11 C12 110.95(13)
C6 C1 C2 118.00(15)
C6 C1 C7 121.41(17)
C2 C1 C7 120.59(17)
C5 C6 C1 121.00(15)
C13 C12 C11 111.20(14)
C14 C13 C12 110.33(14)
C1 C2 C3 121.30(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 N1 1.2341(17)
N2 C8 1.344(2)
N2 C10 1.4687(19)
N2 C14 1.473(2)
O2 N1 1.2450(18)
N1 C9 1.396(2)
C8 C9 1.376(2)
C8 C4 1.498(2)
C5 C6 1.380(2)
C5 C4 1.385(2)
C10 C11 1.520(2)
C3 C2 1.387(2)
C3 C4 1.389(2)
C14 C13 1.516(2)
C11 C12 1.522(3)
C1 C6 1.388(2)
C1 C2 1.385(2)
C1 C7 1.510(2)
C12 C13 1.522(3)
