#------------------------------------------------------------------------------
#$Date: 2016-03-26 14:34:33 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180268 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/54/7115439.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_7115439
loop_
_publ_author_name
'Juanjuan Liu'
'Lanxiang Zhou'
'Weijian Ye'
'Cunde Wang'
_publ_section_title
;
 Formal [3+2] cycloaddition of 1-cyanocyclopropane 1-ester with pyridine,
 quinoline or isoquinoline: a general and efficient strategy for
 construction of cyanoindolizine skeletons
;
_journal_name_full               Chem.Commun.
_journal_page_first              9068
_journal_paper_doi               10.1039/C4cc03267E
_journal_volume                  50
_journal_year                    2014
_chemical_formula_sum            'C22 H13 Cl N2 O'
_chemical_formula_weight         356.79
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 102.951(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   23.071(3)
_cell_length_b                   10.7768(13)
_cell_length_c                   14.3886(19)
_cell_measurement_reflns_used    5829
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.32
_cell_measurement_theta_min      2.43
_cell_volume                     3486.5(8)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0510
_diffrn_reflns_av_sigmaI/netI    0.0511
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            23001
_diffrn_reflns_theta_full        27.54
_diffrn_reflns_theta_max         27.54
_diffrn_reflns_theta_min         2.10
_exptl_absorpt_coefficient_mu    0.232
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1472
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.553
_refine_diff_density_min         -0.476
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         4022
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.1400
_refine_ls_R_factor_gt           0.0698
_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)+(0.1059P)²+4.5018P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1838
_refine_ls_wR_factor_ref         0.2268
_reflns_number_gt                2215
_reflns_number_total             4013
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4cc03267e2.cif
_cod_data_source_block           0509
_cod_original_cell_volume        3486.5(7)
_cod_original_sg_symbol_H-M      'C2/c  '
_cod_database_code               7115439
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.71995(16) 0.6729(3) 0.7682(3) 0.0617(10) Uani 1 1 d .
H1 H 0.7401 0.5975 0.7779 0.074 Uiso 1 1 calc R
C2 C 0.71736(18) 0.7384(4) 0.6867(3) 0.0704(11) Uani 1 1 d .
H2 H 0.7355 0.7073 0.6400 0.084 Uiso 1 1 calc R
C3 C 0.68740(17) 0.8532(3) 0.6725(3) 0.0612(9) Uani 1 1 d .
H3 H 0.6862 0.8976 0.6167 0.073 Uiso 1 1 calc R
C4 C 0.66061(15) 0.8989(3) 0.7386(2) 0.0539(8) Uani 1 1 d .
H4 H 0.6407 0.9745 0.7286 0.065 Uiso 1 1 calc R
C5 C 0.66272(11) 0.8336(2) 0.82145(18) 0.0297(6) Uani 1 1 d .
C6 C 0.63791(14) 0.8634(3) 0.8979(2) 0.0452(7) Uani 1 1 d .
C7 C 0.65053(13) 0.7682(3) 0.9630(2) 0.0445(7) Uani 1 1 d .
C8 C 0.68376(14) 0.6773(3) 0.9255(2) 0.0461(7) Uani 1 1 d .
C9 C 0.63404(14) 0.7704(3) 1.0559(2) 0.0487(8) Uani 1 1 d .
C10 C 0.61484(14) 0.6563(3) 1.0981(2) 0.0466(7) Uani 1 1 d .
C11 C 0.58877(15) 0.5579(3) 1.0431(2) 0.0551(9) Uani 1 1 d .
H11 H 0.5847 0.5598 0.9773 0.066 Uiso 1 1 calc R
C12 C 0.56868(18) 0.4563(3) 1.0854(3) 0.0668(10) Uani 1 1 d .
H12 H 0.5511 0.3904 1.0478 0.080 Uiso 1 1 calc R
C13 C 0.57441(19) 0.4519(3) 1.1818(3) 0.0720(11) Uani 1 1 d .
H13 H 0.5606 0.3835 1.2099 0.086 Uiso 1 1 calc R
C14 C 0.6007(2) 0.5491(4) 1.2371(3) 0.0800(13) Uani 1 1 d .
H14 H 0.6053 0.5459 1.3029 0.096 Uiso 1 1 calc R
C15 C 0.62036(18) 0.6509(3) 1.1960(3) 0.0640(10) Uani 1 1 d .
H15 H 0.6375 0.7168 1.2340 0.077 Uiso 1 1 calc R
C16 C 0.60260(15) 0.9778(3) 0.8974(2) 0.0476(8) Uani 1 1 d .
C17 C 0.63087(17) 1.0934(3) 0.9076(3) 0.0595(9) Uani 1 1 d .
H17 H 0.6720 1.0975 0.9157 0.071 Uiso 1 1 calc R
C18 C 0.54121(15) 0.9759(3) 0.8854(2) 0.0551(9) Uani 1 1 d .
C19 C 0.5985(2) 1.2012(3) 0.9059(3) 0.0720(11) Uani 1 1 d .
H19 H 0.6179 1.2774 0.9143 0.086 Uiso 1 1 calc R
C20 C 0.50876(18) 1.0840(4) 0.8815(3) 0.0719(11) Uani 1 1 d .
H20 H 0.4676 1.0813 0.8719 0.086 Uiso 1 1 calc R
C21 C 0.5382(2) 1.1965(4) 0.8919(3) 0.0762(12) Uani 1 1 d .
H21 H 0.5167 1.2697 0.8893 0.091 Uiso 1 1 calc R
C22 C 0.70684(16) 0.5632(3) 0.9658(3) 0.0577(9) Uani 1 1 d .
Cl1 Cl 0.50414(5) 0.83558(11) 0.87562(8) 0.0827(4) Uani 1 1 d .
N1 N 0.69174(14) 0.7205(3) 0.8380(2) 0.0675(9) Uani 1 1 d .
N2 N 0.72444(17) 0.4694(3) 0.9950(3) 0.0885(12) Uani 1 1 d .
O1 O 0.63530(13) 0.8695(2) 1.09841(17) 0.0673(7) Uani 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
C2 C1 N1 119.1(3)
C1 C2 C3 120.5(3)
C4 C3 C2 120.6(3)
C3 C4 C5 119.6(3)
C4 C5 N1 121.4(3)
C4 C5 C6 128.9(3)
N1 C5 C6 109.7(2)
C7 C6 C5 107.7(3)
C7 C6 C16 131.2(3)
C5 C6 C16 121.0(3)
C6 C7 C8 107.8(3)
C6 C7 C9 123.3(3)
C8 C7 C9 128.9(3)
N1 C8 C22 123.3(3)
N1 C8 C7 107.7(3)
C22 C8 C7 129.0(3)
O1 C9 C7 119.0(3)
O1 C9 C10 119.5(3)
C7 C9 C10 121.5(3)
C11 C10 C15 118.6(3)
C11 C10 C9 122.4(3)
C15 C10 C9 118.9(3)
C10 C11 C12 120.2(3)
C13 C12 C11 120.7(3)
C12 C13 C14 119.4(3)
C15 C14 C13 120.5(4)
C14 C15 C10 120.5(3)
C18 C16 C17 117.7(3)
C18 C16 C6 122.3(3)
C17 C16 C6 120.0(3)
C19 C17 C16 120.8(4)
C20 C18 C16 121.4(3)
C20 C18 Cl1 118.8(3)
C16 C18 Cl1 119.8(3)
C21 C19 C17 120.1(4)
C18 C20 C21 119.2(4)
C19 C21 C20 120.8(4)
N2 C22 C8 177.4(5)
C5 N1 C8 107.0(3)
C5 N1 C1 118.8(3)
C8 N1 C1 134.2(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.358(5)
C1 N1 1.410(4)
C2 C3 1.410(5)
C3 C4 1.339(5)
C4 C5 1.376(4)
C5 N1 1.384(4)
C5 C6 1.388(4)
C6 C7 1.376(4)
C6 C16 1.476(4)
C7 C8 1.423(4)
C7 C9 1.469(4)
C8 N1 1.393(4)
C8 C22 1.412(5)
C9 O1 1.229(4)
C9 C10 1.482(4)
C10 C11 1.379(5)
C10 C15 1.387(5)
C11 C12 1.382(5)
C12 C13 1.364(6)
C13 C14 1.371(6)
C14 C15 1.370(5)
C16 C18 1.388(5)
C16 C17 1.398(5)
C17 C19 1.378(5)
C18 C20 1.380(5)
C18 Cl1 1.727(4)
C19 C21 1.361(6)
C20 C21 1.381(6)
C22 N2 1.134(4)
