#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/47/4024740.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_4024740
loop_
_publ_author_name
'Xiang-Ying Tang'
'Min Shi'
_publ_section_title
;
An Efficient Route to 2-Substituted N-(1-Amino-3-methylpyrrol)amides by
Ring-Opening Cyclization of Benzylidene- and
Alkylidenecyclopropylcarbaldehydes with Hydrazides
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5983
_journal_page_last               5986
_journal_paper_doi               10.1021/jo900730t
_journal_volume                  74
_journal_year                    2009
_chemical_formula_sum            'C19 H13 Cl N2 O2'
_chemical_formula_weight         336.76
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_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                96.694(2)
_cell_angle_beta                 97.449(2)
_cell_angle_gamma                100.456(2)
_cell_formula_units_Z            2
_cell_length_a                   5.9212(8)
_cell_length_b                   9.7223(13)
_cell_length_c                   14.6666(19)
_cell_measurement_reflns_used    2573
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      56.382
_cell_measurement_theta_min      5.482
_cell_volume                     814.75(19)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.1050
_diffrn_reflns_av_sigmaI/netI    0.0725
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            4487
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.15
_exptl_absorpt_coefficient_mu    0.248
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78385
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             348
_exptl_crystal_size_max          0.379
_exptl_crystal_size_mid          0.236
_exptl_crystal_size_min          0.152
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.441
_refine_diff_density_rms         0.067
_refine_ls_extinction_coef       0.037(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3138
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0630
_refine_ls_R_factor_gt           0.0576
_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)+(0.0872P)²+0.1453P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1525
_refine_ls_wR_factor_ref         0.1575
_reflns_number_gt                2783
_reflns_number_total             3138
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo900730t_si_001.cif
_cod_data_source_block           cd28568
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4024740
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 1.20659(11) 0.57078(6) 0.70836(5) 0.0622(3) Uani 1 1 d . . .
N1 N 0.4304(3) 0.02802(17) 0.82391(11) 0.0408(4) Uani 1 1 d . . .
N2 N 0.4612(3) -0.03290(17) 0.73745(11) 0.0399(4) Uani 1 1 d . . .
O1 O 0.7462(3) -0.15244(16) 0.78788(10) 0.0504(4) Uani 1 1 d . . .
O2 O 0.1497(3) 0.02770(19) 0.65024(12) 0.0607(5) Uani 1 1 d . . .
C1 C 0.2749(4) -0.0356(2) 0.87479(15) 0.0489(5) Uani 1 1 d . . .
H1 H 0.1849 -0.1264 0.8601 0.059 Uiso 1 1 calc R . .
C2 C 0.2765(4) 0.0580(3) 0.95030(16) 0.0528(6) Uani 1 1 d . . .
H2 H 0.1885 0.0423 0.9976 0.063 Uiso 1 1 calc R . .
C3 C 0.4338(4) 0.1835(2) 0.94578(14) 0.0464(5) Uani 1 1 d . . .
C4 C 0.5289(3) 0.16540(19) 0.86573(13) 0.0370(4) Uani 1 1 d . . .
C5 C 0.6989(3) 0.26155(19) 0.82722(12) 0.0352(4) Uani 1 1 d . . .
C6 C 0.6735(4) 0.4020(2) 0.82628(13) 0.0398(4) Uani 1 1 d . . .
H6 H 0.5480 0.4312 0.8492 0.048 Uiso 1 1 calc R . .
C7 C 0.8308(4) 0.4979(2) 0.79206(14) 0.0430(5) Uani 1 1 d . . .
H7 H 0.8137 0.5912 0.7928 0.052 Uiso 1 1 calc R . .
C8 C 1.0134(3) 0.4529(2) 0.75694(14) 0.0416(5) Uani 1 1 d . . .
C9 C 1.0453(3) 0.3160(2) 0.75671(15) 0.0444(5) Uani 1 1 d . . .
H9 H 1.1701 0.2876 0.7327 0.053 Uiso 1 1 calc R . .
C10 C 0.8887(3) 0.2213(2) 0.79282(14) 0.0407(5) Uani 1 1 d . . .
H10 H 0.9110 0.1292 0.7941 0.049 Uiso 1 1 calc R . .
C11 C 0.6142(3) -0.1261(2) 0.72666(13) 0.0386(4) Uani 1 1 d . . .
C12 C 0.3060(4) -0.0344(2) 0.65592(14) 0.0416(5) Uani 1 1 d . . .
C13 C 0.3846(3) -0.1286(2) 0.58450(14) 0.0421(5) Uani 1 1 d . . .
C14 C 0.5678(3) -0.1809(2) 0.62608(14) 0.0406(5) Uani 1 1 d . . .
C15 C 0.6769(4) -0.2712(2) 0.57659(17) 0.0542(6) Uani 1 1 d . . .
H15 H 0.8002 -0.3062 0.6048 0.065 Uiso 1 1 calc R . .
C16 C 0.5932(5) -0.3074(3) 0.48219(18) 0.0653(7) Uani 1 1 d . . .
H16 H 0.6626 -0.3679 0.4462 0.078 Uiso 1 1 calc R . .
C17 C 0.4101(5) -0.2558(3) 0.44058(17) 0.0651(7) Uani 1 1 d . . .
H17 H 0.3585 -0.2826 0.3772 0.078 Uiso 1 1 calc R . .
C18 C 0.3010(4) -0.1652(3) 0.49062(15) 0.0554(6) Uani 1 1 d . . .
H18 H 0.1772 -0.1305 0.4625 0.067 Uiso 1 1 calc R . .
C19 C 0.4885(6) 0.3109(3) 1.01832(17) 0.0758(9) Uani 1 1 d . . .
H19A H 0.6410 0.3636 1.0162 0.114 Uiso 1 1 calc R . .
H19B H 0.4835 0.2819 1.0785 0.114 Uiso 1 1 calc R . .
H19C H 0.3762 0.3693 1.0069 0.114 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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 N2 123.18(17) . . ?
C1 N1 C4 110.70(16) . . ?
N2 N1 C4 125.70(16) . . ?
N1 N2 C11 122.29(16) . . ?
N1 N2 C12 122.67(17) . . ?
C11 N2 C12 113.39(16) . . ?
C2 C1 N1 107.06(19) . . ?
C2 C1 H1 126.5 . . ?
N1 C1 H1 126.5 . . ?
C1 C2 C3 108.64(19) . . ?
C1 C2 H2 125.7 . . ?
C3 C2 H2 125.7 . . ?
C4 C3 C2 108.21(18) . . ?
C4 C3 C19 127.1(2) . . ?
C2 C3 C19 124.6(2) . . ?
C3 C4 N1 105.35(17) . . ?
C3 C4 C5 130.86(17) . . ?
N1 C4 C5 123.78(16) . . ?
C10 C5 C6 117.95(18) . . ?
C10 C5 C4 123.08(17) . . ?
C6 C5 C4 118.96(17) . . ?
C7 C6 C5 121.41(17) . . ?
C7 C6 H6 119.3 . . ?
C5 C6 H6 119.3 . . ?
C8 C7 C6 118.72(18) . . ?
C8 C7 H7 120.6 . . ?
C6 C7 H7 120.6 . . ?
C7 C8 C9 121.80(19) . . ?
C7 C8 Cl1 119.32(16) . . ?
C9 C8 Cl1 118.86(16) . . ?
C8 C9 C10 118.99(18) . . ?
C8 C9 H9 120.5 . . ?
C10 C9 H9 120.5 . . ?
C9 C10 C5 121.09(18) . . ?
C9 C10 H10 119.5 . . ?
C5 C10 H10 119.5 . . ?
O1 C11 N2 125.32(18) . . ?
O1 C11 C14 130.43(19) . . ?
N2 C11 C14 104.24(16) . . ?
O2 C12 N2 125.31(19) . . ?
O2 C12 C13 130.73(19) . . ?
N2 C12 C13 103.96(17) . . ?
C14 C13 C18 121.4(2) . . ?
C14 C13 C12 108.99(17) . . ?
C18 C13 C12 129.6(2) . . ?
C15 C14 C13 122.0(2) . . ?
C15 C14 C11 128.9(2) . . ?
C13 C14 C11 109.06(17) . . ?
C14 C15 C16 116.5(2) . . ?
C14 C15 H15 121.7 . . ?
C16 C15 H15 121.7 . . ?
C17 C16 C15 121.6(2) . . ?
C17 C16 H16 119.2 . . ?
C15 C16 H16 119.2 . . ?
C16 C17 C18 121.6(2) . . ?
C16 C17 H17 119.2 . . ?
C18 C17 H17 119.2 . . ?
C17 C18 C13 116.8(2) . . ?
C17 C18 H18 121.6 . . ?
C13 C18 H18 121.6 . . ?
C3 C19 H19A 109.5 . . ?
C3 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C3 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C8 1.748(2) . ?
N1 C1 1.366(3) . ?
N1 N2 1.384(2) . ?
N1 C4 1.391(2) . ?
N2 C11 1.403(3) . ?
N2 C12 1.408(3) . ?
O1 C11 1.194(2) . ?
O2 C12 1.192(2) . ?
C1 C2 1.347(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.408(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.373(3) . ?
C3 C19 1.493(3) . ?
C4 C5 1.461(3) . ?
C5 C10 1.390(3) . ?
C5 C6 1.402(3) . ?
C6 C7 1.380(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.375(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.377(3) . ?
C9 C10 1.385(3) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 C14 1.481(3) . ?
C12 C13 1.487(3) . ?
C13 C14 1.382(3) . ?
C13 C18 1.383(3) . ?
C14 C15 1.377(3) . ?
C15 C16 1.390(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.378(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.382(4) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 N1 N2 C11 -86.6(2) . . . . ?
C4 N1 N2 C11 101.4(2) . . . . ?
C1 N1 N2 C12 77.8(3) . . . . ?
C4 N1 N2 C12 -94.2(2) . . . . ?
N2 N1 C1 C2 -174.62(19) . . . . ?
C4 N1 C1 C2 -1.6(2) . . . . ?
N1 C1 C2 C3 0.9(3) . . . . ?
C1 C2 C3 C4 0.1(3) . . . . ?
C1 C2 C3 C19 -178.3(2) . . . . ?
C2 C3 C4 N1 -1.0(2) . . . . ?
C19 C3 C4 N1 177.3(2) . . . . ?
C2 C3 C4 C5 179.6(2) . . . . ?
C19 C3 C4 C5 -2.0(4) . . . . ?
C1 N1 C4 C3 1.6(2) . . . . ?
N2 N1 C4 C3 174.43(19) . . . . ?
C1 N1 C4 C5 -178.96(18) . . . . ?
N2 N1 C4 C5 -6.2(3) . . . . ?
C3 C4 C5 C10 133.5(2) . . . . ?
N1 C4 C5 C10 -45.7(3) . . . . ?
C3 C4 C5 C6 -45.2(3) . . . . ?
N1 C4 C5 C6 135.6(2) . . . . ?
C10 C5 C6 C7 0.2(3) . . . . ?
C4 C5 C6 C7 179.00(17) . . . . ?
C5 C6 C7 C8 1.1(3) . . . . ?
C6 C7 C8 C9 -1.3(3) . . . . ?
C6 C7 C8 Cl1 177.03(15) . . . . ?
C7 C8 C9 C10 0.1(3) . . . . ?
Cl1 C8 C9 C10 -178.22(15) . . . . ?
C8 C9 C10 C5 1.3(3) . . . . ?
C6 C5 C10 C9 -1.5(3) . . . . ?
C4 C5 C10 C9 179.84(17) . . . . ?
N1 N2 C11 O1 -7.1(3) . . . . ?
C12 N2 C11 O1 -172.83(19) . . . . ?
N1 N2 C11 C14 172.04(16) . . . . ?
C12 N2 C11 C14 6.3(2) . . . . ?
N1 N2 C12 O2 8.4(3) . . . . ?
C11 N2 C12 O2 174.1(2) . . . . ?
N1 N2 C12 C13 -171.26(17) . . . . ?
C11 N2 C12 C13 -5.6(2) . . . . ?
O2 C12 C13 C14 -177.2(2) . . . . ?
N2 C12 C13 C14 2.5(2) . . . . ?
O2 C12 C13 C18 2.7(4) . . . . ?
N2 C12 C13 C18 -177.6(2) . . . . ?
C18 C13 C14 C15 0.3(3) . . . . ?
C12 C13 C14 C15 -179.82(19) . . . . ?
C18 C13 C14 C11 -178.68(19) . . . . ?
C12 C13 C14 C11 1.2(2) . . . . ?
O1 C11 C14 C15 -4.2(4) . . . . ?
N2 C11 C14 C15 176.7(2) . . . . ?
O1 C11 C14 C13 174.6(2) . . . . ?
N2 C11 C14 C13 -4.4(2) . . . . ?
C13 C14 C15 C16 0.0(3) . . . . ?
C11 C14 C15 C16 178.7(2) . . . . ?
C14 C15 C16 C17 -0.2(4) . . . . ?
C15 C16 C17 C18 0.2(4) . . . . ?
C16 C17 C18 C13 0.1(4) . . . . ?
C14 C13 C18 C17 -0.3(3) . . . . ?
C12 C13 C18 C17 179.8(2) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30659013
