#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:54:51 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180322 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/36/7153680.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_7153680
loop_
_publ_author_name
'Xin, Xiaoqing'
'Zhang, Qian'
'Liang, Yongjiu'
'Zhang, Rui'
'Dong, Dewen'
_publ_section_title
;
 Tandem halogenation/Michael-initiated ring-closing reaction of
 α,β-unsaturated nitriles and activated methylene compounds: one-pot
 diastereoselective synthesis of functionalized cyclopropanes.
;
_journal_issue                   15
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              2427
_journal_page_last               2435
_journal_paper_doi               10.1039/c4ob00087k
_journal_volume                  12
_journal_year                    2014
_chemical_formula_moiety         'C17 H16 Cl N O4'
_chemical_formula_sum            'C17 H16 Cl N O4'
_chemical_formula_weight         333.76
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                93.206(2)
_cell_angle_beta                 102.273(2)
_cell_angle_gamma                104.014(2)
_cell_formula_units_Z            2
_cell_length_a                   7.7069(10)
_cell_length_b                   10.4968(14)
_cell_length_c                   11.1874(15)
_cell_measurement_temperature    293(2)
_cell_volume                     852.5(2)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.974
_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  0.0190
_diffrn_reflns_av_sigmaI/netI    0.0358
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4655
_diffrn_reflns_theta_full        26.05
_diffrn_reflns_theta_max         26.05
_diffrn_reflns_theta_min         1.87
_exptl_absorpt_coefficient_mu    0.242
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             348
_refine_diff_density_max         0.423
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     206
_refine_ls_number_reflns         3285
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0763
_refine_ls_R_factor_gt           0.0631
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0926P)²+0.2763P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1618
_refine_ls_wR_factor_ref         0.1744
_reflns_number_gt                2642
_reflns_number_total             3285
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ob00087k2.cif
_cod_data_source_block           x
_cod_database_code               7153680
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Cl1 Cl 1.41544(11) 0.99031(8) 0.67720(8) 0.0755(3) Uani 1 1 d .
O4 O 0.3864(2) 0.75000(18) 0.10603(16) 0.0486(5) Uani 1 1 d .
O2 O 0.8223(3) 0.5142(2) 0.12087(18) 0.0580(5) Uani 1 1 d .
C11 C 0.4174(3) 0.6817(2) 0.1997(2) 0.0414(6) Uani 1 1 d .
O3 O 0.3072(3) 0.6309(2) 0.25494(19) 0.0626(6) Uani 1 1 d .
C4 C 0.8770(3) 0.7435(2) 0.4389(2) 0.0378(5) Uani 1 1 d .
C5 C 0.8825(3) 0.8164(2) 0.5479(2) 0.0409(6) Uani 1 1 d .
H5 H 0.7735 0.8125 0.5724 0.049 Uiso 1 1 calc R
C9 C 0.6146(3) 0.6757(2) 0.2317(2) 0.0380(5) Uani 1 1 d .
C7 C 0.6953(3) 0.6599(2) 0.3686(2) 0.0389(5) Uani 1 1 d .
H7 H 0.6023 0.6477 0.4176 0.047 Uiso 1 1 calc R
C6 C 1.0460(4) 0.8949(2) 0.6209(2) 0.0449(6) Uani 1 1 d .
H6 H 1.0475 0.9441 0.6930 0.054 Uiso 1 1 calc R
N1 N 0.8336(3) 0.8314(2) 0.1256(2) 0.0524(6) Uani 1 1 d .
C1 C 1.2064(4) 0.8981(2) 0.5840(2) 0.0465(6) Uani 1 1 d .
O1 O 0.4774(3) 0.3895(2) 0.3680(2) 0.0766(7) Uani 1 1 d .
C3 C 1.0409(3) 0.7526(3) 0.4032(2) 0.0453(6) Uani 1 1 d .
H3 H 1.0398 0.7069 0.3292 0.054 Uiso 1 1 calc R
C14 C 0.8048(4) 0.4996(2) 0.2233(2) 0.0444(6) Uani 1 1 d .
C8 C 0.6574(3) 0.5474(2) 0.2711(2) 0.0388(5) Uani 1 1 d .
C2 C 1.2064(4) 0.8287(3) 0.4762(2) 0.0491(6) Uani 1 1 d .
H2 H 1.3160 0.8327 0.4525 0.059 Uiso 1 1 calc R
C16 C 0.4969(4) 0.4278(3) 0.2726(2) 0.0501(6) Uani 1 1 d .
C12 C 0.2033(4) 0.7706(3) 0.0700(3) 0.0624(8) Uani 1 1 d .
H12A H 0.1679 0.8034 0.1416 0.075 Uiso 1 1 calc R
H12B H 0.1146 0.6878 0.0340 0.075 Uiso 1 1 calc R
C15 C 0.9121(5) 0.4262(3) 0.3078(3) 0.0706(9) Uani 1 1 d .
H15A H 1.0081 0.4079 0.2728 0.106 Uiso 1 1 calc R
H15B H 0.8319 0.3445 0.3192 0.106 Uiso 1 1 calc R
H15C H 0.9653 0.4788 0.3860 0.106 Uiso 1 1 calc R
C17 C 0.3850(5) 0.3575(3) 0.1497(3) 0.0767(10) Uani 1 1 d .
H17A H 0.4627 0.3242 0.1064 0.115 Uiso 1 1 calc R
H17B H 0.3317 0.4180 0.1026 0.115 Uiso 1 1 calc R
H17C H 0.2889 0.2853 0.1616 0.115 Uiso 1 1 calc R
C13 C 0.2066(5) 0.8668(5) -0.0199(4) 0.0932(13) Uani 1 1 d .
H13A H 0.2890 0.9500 0.0181 0.140 Uiso 1 1 calc R
H13B H 0.0852 0.8780 -0.0483 0.140 Uiso 1 1 calc R
H13C H 0.2478 0.8356 -0.0884 0.140 Uiso 1 1 calc R
C10 C 0.7364(3) 0.7601(2) 0.1697(2) 0.0373(5) 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'
Cl Cl 0.1484 0.1585 '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
C11 O4 C12 116.9(2)
O3 C11 O4 126.0(2)
O3 C11 C9 122.9(2)
O4 C11 C9 111.1(2)
C3 C4 C5 118.1(2)
C3 C4 C7 124.3(2)
C5 C4 C7 117.6(2)
C6 C5 C4 121.7(2)
C10 C9 C11 115.7(2)
C10 C9 C8 118.9(2)
C11 C9 C8 118.8(2)
C10 C9 C7 116.8(2)
C11 C9 C7 116.35(19)
C8 C9 C7 57.69(14)
C4 C7 C8 127.9(2)
C4 C7 C9 121.89(19)
C8 C7 C9 60.09(15)
C1 C6 C5 118.3(2)
C2 C1 C6 121.7(2)
C2 C1 Cl1 118.9(2)
C6 C1 Cl1 119.4(2)
C2 C3 C4 121.0(2)
O2 C14 C15 123.3(3)
O2 C14 C8 120.5(2)
C15 C14 C8 116.1(2)
C7 C8 C14 124.8(2)
C7 C8 C9 62.22(15)
C14 C8 C9 118.92(19)
C7 C8 C16 116.5(2)
C14 C8 C16 109.1(2)
C9 C8 C16 118.8(2)
C1 C2 C3 119.1(2)
O1 C16 C17 123.6(3)
O1 C16 C8 119.5(2)
C17 C16 C8 116.6(2)
O4 C12 C13 108.2(3)
N1 C10 C9 176.5(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C1 1.742(3)
O4 C11 1.316(3)
O4 C12 1.454(3)
O2 C14 1.196(3)
C11 O3 1.195(3)
C11 C9 1.503(3)
C4 C3 1.387(3)
C4 C5 1.390(3)
C4 C7 1.486(3)
C5 C6 1.385(3)
C9 C10 1.446(3)
C9 C8 1.528(3)
C9 C7 1.560(3)
C7 C8 1.490(3)
C6 C1 1.378(4)
N1 C10 1.136(3)
C1 C2 1.374(4)
O1 C16 1.188(3)
C3 C2 1.387(4)
C14 C15 1.494(4)
C14 C8 1.527(3)
C8 C16 1.538(3)
C16 C17 1.501(4)
C12 C13 1.465(5)
