#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/22/1512221.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_1512221
loop_
_publ_author_name
'Trita, Andrada Stefania'
'Roisnel, Thierry'
'Mongin, Florence'
'Chevallier, Floris'
_publ_section_title
;
 Hydrogen Bond Templated 1:1 Macrocyclization through an Olefin
 Metathesis/Hydrogenation Sequence
;
_journal_issue                   14
_journal_name_full               'Organic Letters'
_journal_page_first              3798
_journal_paper_doi               10.1021/ol401803t
_journal_volume                  15
_journal_year                    2013
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C10 H8 N2, C6 H4 Cl2 O2'
_chemical_formula_sum            'C16 H12 Cl2 N2 O2'
_chemical_formula_weight         335.18
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      15
_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
_cell_angle_alpha                90
_cell_angle_beta                 94.889(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   14.1033(10)
_cell_length_b                   10.5860(9)
_cell_length_c                   20.4253(17)
_cell_measurement_reflns_used    2590
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.11
_cell_measurement_theta_min      2.56
_cell_measurement_wavelength     0.71073
_cell_volume                     3038.4(4)
_computing_cell_refinement       'Bruker APEX2 (Bruker, 2006)'
_computing_data_collection       'Bruker APEX2 (Bruker, 2006)'
_computing_data_reduction        'Bruker APEX2 (Bruker, 2006)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material
;
           WinGX publication routines (Farrugia, 2012),
           CRYSCAL (T. Roisnel, local program)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.99
_diffrn_measured_fraction_theta_max 0.99
_diffrn_measurement_device_type  'APEXII, Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thin slices'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0354
_diffrn_reflns_av_unetI/netI     0.0356
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            12321
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.05
_exptl_absorpt_coefficient_mu    0.435
_exptl_absorpt_correction_T_max  0.953
_exptl_absorpt_correction_T_min  0.792
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
  [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.465
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1376
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.262
_refine_diff_density_min         -0.396
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     205
_refine_ls_number_reflns         3463
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.111
_refine_ls_R_factor_all          0.0636
_refine_ls_R_factor_gt           0.0395
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0464P)²+0.8673P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0965
_refine_ls_wR_factor_ref         0.1085
_reflns_number_gt                2455
_reflns_number_total             3463
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol401803t_si_002.cif
_cod_data_source_block           (4,6-diCl-res)2.(3c)2
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               1512221
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 0.34681(14) 0.78312(19) 0.23430(9) 0.0413(4) Uani 1 1 d .
C2 C 0.36820(13) 0.68672(17) 0.19206(8) 0.0363(4) Uani 1 1 d .
C3 C 0.41948(12) 0.71628(17) 0.13901(9) 0.0371(4) Uani 1 1 d .
H3 H 0.4343 0.6525 0.1103 0.044 Uiso 1 1 calc R
C4 C 0.44909(12) 0.83843(18) 0.12795(9) 0.0356(4) Uani 1 1 d .
C5 C 0.42652(13) 0.93330(18) 0.17108(9) 0.0390(4) Uani 1 1 d .
C6 C 0.37505(14) 0.90566(18) 0.22399(9) 0.0435(5) Uani 1 1 d .
H6 H 0.3596 0.9695 0.2525 0.052 Uiso 1 1 calc R
O7 O 0.33679(11) 0.56815(13) 0.20365(7) 0.0509(4) Uani 1 1 d .
H7 H 0.3399(17) 0.527(3) 0.1681(13) 0.076 Uiso 1 1 d .
O8 O 0.49941(10) 0.86943(14) 0.07641(7) 0.0476(4) Uani 1 1 d .
H8 H 0.4970(16) 0.810(3) 0.0470(12) 0.071 Uiso 1 1 d .
Cl1 Cl 0.28057(5) 0.75042(6) 0.29981(3) 0.0745(2) Uani 1 1 d .
Cl2 Cl 0.46457(4) 1.08651(5) 0.15861(3) 0.05638(18) Uani 1 1 d .
N11 N 0.31906(11) 0.44246(14) 0.08503(7) 0.0376(4) Uani 1 1 d .
C12 C 0.22846(14) 0.46709(19) 0.06449(10) 0.0446(5) Uani 1 1 d .
H12 H 0.189 0.4981 0.095 0.054 Uiso 1 1 calc R
C13 C 0.19007(14) 0.4493(2) 0.00093(10) 0.0462(5) Uani 1 1 d .
H13 H 0.1264 0.467 -0.0112 0.055 Uiso 1 1 calc R
C14 C 0.24901(14) 0.4045(2) -0.04391(10) 0.0484(5) Uani 1 1 d .
H14 H 0.226 0.3927 -0.0875 0.058 Uiso 1 1 calc R
C15 C 0.34186(14) 0.37721(19) -0.02398(9) 0.0423(5) Uani 1 1 d .
H15 H 0.382 0.3462 -0.054 0.051 Uiso 1 1 calc R
C16 C 0.37625(12) 0.39594(15) 0.04124(8) 0.0327(4) Uani 1 1 d .
C17 C 0.47594(12) 0.36779(16) 0.06529(9) 0.0348(4) Uani 1 1 d .
N18 N 0.52929(11) 0.30977(15) 0.02279(8) 0.0422(4) Uani 1 1 d .
C19 C 0.62040(15) 0.2858(2) 0.04216(11) 0.0528(5) Uani 1 1 d .
H19 H 0.6572 0.2457 0.0127 0.063 Uiso 1 1 calc R
C20 C 0.66275(15) 0.3169(2) 0.10287(12) 0.0587(6) Uani 1 1 d .
H20 H 0.7268 0.2998 0.114 0.07 Uiso 1 1 calc R
C21 C 0.60850(16) 0.3739(2) 0.14679(11) 0.0575(6) Uani 1 1 d .
H21 H 0.6349 0.3958 0.1885 0.069 Uiso 1 1 calc R
C22 C 0.51411(15) 0.39825(19) 0.12824(10) 0.0461(5) Uani 1 1 d .
H22 H 0.4759 0.4351 0.1579 0.055 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 0 '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 0.006 '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
C6 C1 C2 121.12(17)
C6 C1 Cl1 119.22(14)
C2 C1 Cl1 119.63(15)
O7 C2 C1 118.70(16)
O7 C2 C3 122.92(16)
C1 C2 C3 118.37(17)
C4 C3 C2 121.51(17)
C4 C3 H3 119.2
C2 C3 H3 119.2
O8 C4 C3 122.48(16)
O8 C4 C5 118.63(17)
C3 C4 C5 118.89(16)
C6 C5 C4 120.38(17)
C6 C5 Cl2 120.14(15)
C4 C5 Cl2 119.47(14)
C1 C6 C5 119.73(17)
C1 C6 H6 120.1
C5 C6 H6 120.1
C2 O7 H7 106.2(18)
C4 O8 H8 111.5(16)
C12 N11 C16 118.25(16)
N11 C12 C13 123.94(17)
N11 C12 H12 118
C13 C12 H12 118
C14 C13 C12 117.70(18)
C14 C13 H13 121.1
C12 C13 H13 121.1
C15 C14 C13 119.52(19)
C15 C14 H14 120.2
C13 C14 H14 120.2
C14 C15 C16 120.07(17)
C14 C15 H15 120
C16 C15 H15 120
N11 C16 C15 120.50(17)
N11 C16 C17 117.31(15)
C15 C16 C17 122.18(15)
N18 C17 C22 120.64(17)
N18 C17 C16 116.48(15)
C22 C17 C16 122.88(16)
C19 N18 C17 118.19(17)
N18 C19 C20 123.8(2)
N18 C19 H19 118.1
C20 C19 H19 118.1
C21 C20 C19 118.3(2)
C21 C20 H20 120.8
C19 C20 H20 120.8
C20 C21 C22 118.9(2)
C20 C21 H21 120.5
C22 C21 H21 120.5
C21 C22 C17 120.03(19)
C21 C22 H22 120
C17 C22 H22 120
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C6 1.378(3)
C1 C2 1.386(3)
C1 Cl1 1.7311(18)
C2 O7 1.358(2)
C2 C3 1.389(2)
C3 C4 1.383(3)
C3 H3 0.93
C4 O8 1.359(2)
C4 C5 1.391(3)
C5 C6 1.384(3)
C5 Cl2 1.734(2)
C6 H6 0.93
O7 H7 0.85(3)
O8 H8 0.87(3)
N11 C12 1.336(2)
N11 C16 1.348(2)
C12 C13 1.376(3)
C12 H12 0.93
C13 C14 1.373(3)
C13 H13 0.93
C14 C15 1.369(3)
C14 H14 0.93
C15 C16 1.393(2)
C15 H15 0.93
C16 C17 1.480(2)
C17 N18 1.345(2)
C17 C22 1.389(3)
N18 C19 1.336(2)
C19 C20 1.370(3)
C19 H19 0.93
C20 C21 1.368(3)
C20 H20 0.93
C21 C22 1.377(3)
C21 H21 0.93
C22 H22 0.93
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O7 H7 N11 0.85(3) 1.92(3) 2.757(2) 168(2) .
O8 H8 N18 0.87(3) 1.92(3) 2.780(2) 170(2) 5_665
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
C6 C1 C2 O7 -178.52(17)
Cl1 C1 C2 O7 -0.4(3)
C6 C1 C2 C3 0.4(3)
Cl1 C1 C2 C3 178.47(13)
O7 C2 C3 C4 178.90(17)
C1 C2 C3 C4 0.1(3)
C2 C3 C4 O8 179.93(16)
C2 C3 C4 C5 -0.1(3)
O8 C4 C5 C6 179.72(17)
C3 C4 C5 C6 -0.2(3)
O8 C4 C5 Cl2 -1.0(2)
C3 C4 C5 Cl2 179.08(14)
C2 C1 C6 C5 -0.7(3)
Cl1 C1 C6 C5 -178.82(15)
C4 C5 C6 C1 0.6(3)
Cl2 C5 C6 C1 -178.65(15)
C16 N11 C12 C13 -0.8(3)
N11 C12 C13 C14 -0.6(3)
C12 C13 C14 C15 1.2(3)
C13 C14 C15 C16 -0.5(3)
C12 N11 C16 C15 1.5(3)
C12 N11 C16 C17 -179.21(15)
C14 C15 C16 N11 -0.9(3)
C14 C15 C16 C17 179.90(17)
N11 C16 C17 N18 173.54(15)
C15 C16 C17 N18 -7.2(2)
N11 C16 C17 C22 -6.2(3)
C15 C16 C17 C22 173.00(18)
C22 C17 N18 C19 -2.0(3)
C16 C17 N18 C19 178.25(16)
C17 N18 C19 C20 0.0(3)
N18 C19 C20 C21 1.2(4)
C19 C20 C21 C22 -0.4(4)
C20 C21 C22 C17 -1.5(3)
N18 C17 C22 C21 2.7(3)
C16 C17 C22 C21 -177.49(18)
