#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:16:33 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178428 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/49/4024964.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_4024964
loop_
_publ_author_name
'Ines Bergner'
'Christine Wiebe'
'Nino Meyer'
'Till Opatz'
_publ_section_title
;
Cyclocondensation of α-Aminonitriles and Enones: A Short Access to
3,4-Dihydro-2H-pyrrole 2-carbonitriles and 2,3,5-Trisubstituted Pyrroles
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8243
_journal_page_last               8253
_journal_paper_doi               10.1021/jo901759u
_journal_volume                  74
_journal_year                    2009
_chemical_formula_sum            'C19 H14 N2 O'
_chemical_formula_weight         286.32
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_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                 109.68(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   19.205(15)
_cell_length_b                   5.6691(7)
_cell_length_c                   14.706(10)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      29
_cell_measurement_theta_min      21
_cell_volume                     1507.6(15)
_computing_cell_refinement       'Enraf Nonius Software V5'
_computing_data_collection       'Enraf Nonius Software V5'
_computing_data_reduction        'Corinc (Dräger, 1971)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR-97 (Altomare, 1997)'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'CAD4 Enraf Nonius'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0499
_diffrn_reflns_av_sigmaI/netI    0.0807
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2981
_diffrn_reflns_theta_full        70.33
_diffrn_reflns_theta_max         70.33
_diffrn_reflns_theta_min         2.44
_diffrn_source                   'rotating anode'
_diffrn_standards_decay_%        3
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.628
_exptl_absorpt_correction_T_max  0.8847
_exptl_absorpt_correction_T_min  0.8101
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   'Corinc (Dräger, 1971)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2856
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.1392
_refine_ls_R_factor_gt           0.0720
_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)+(0.0960P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_obs         0.1714
_refine_ls_wR_factor_ref         0.2071
_reflns_number_gt                1632
_reflns_number_total             2856
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo901759u_si_002.cif
_cod_data_source_block           cw14
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4024964
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
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.31039(16) 0.2785(5) 0.3775(2) 0.0418(7) Uani 1 1 d . . .
C2 C 0.34298(18) 0.4531(6) 0.3553(2) 0.0364(8) Uani 1 1 d . . .
C3 C 0.29591(18) 0.6633(6) 0.3117(3) 0.0421(9) Uani 1 1 d . . .
H3A H 0.2875 0.6755 0.2417 0.051 Uiso 1 1 calc R . .
H3B H 0.3187 0.8114 0.3439 0.051 Uiso 1 1 calc R . .
C4 C 0.22425(19) 0.6101(6) 0.3306(3) 0.0409(9) Uani 1 1 d . . .
H4 H 0.2259 0.6921 0.3915 0.049 Uiso 1 1 calc R . .
C5 C 0.2314(2) 0.3389(6) 0.3509(3) 0.0443(9) Uani 1 1 d . . .
H5 H 0.2033 0.2530 0.2903 0.053 Uiso 1 1 calc R . .
C6 C 0.42085(19) 0.4499(6) 0.3661(2) 0.0360(8) Uani 1 1 d . . .
O7 O 0.46157(12) 0.2537(4) 0.40768(16) 0.0373(6) Uani 1 1 d . . .
C8 C 0.53137(19) 0.2936(6) 0.4049(2) 0.0361(8) Uani 1 1 d . . .
C9 C 0.5904(2) 0.1429(6) 0.4398(2) 0.0425(9) Uani 1 1 d . . .
H9 H 0.5868 -0.0029 0.4697 0.051 Uiso 1 1 calc R . .
C10 C 0.6553(2) 0.2173(7) 0.4286(3) 0.0462(9) Uani 1 1 d . . .
H10 H 0.6976 0.1185 0.4509 0.055 Uiso 1 1 calc R . .
C11 C 0.6612(2) 0.4315(7) 0.3858(3) 0.0449(9) Uani 1 1 d . . .
H11 H 0.7072 0.4753 0.3798 0.054 Uiso 1 1 calc R . .
C12 C 0.60137(19) 0.5821(6) 0.3518(2) 0.0404(8) Uani 1 1 d . . .
H12 H 0.6054 0.7283 0.3224 0.048 Uiso 1 1 calc R . .
C13 C 0.53451(18) 0.5110(6) 0.3624(2) 0.0337(8) Uani 1 1 d . . .
C14 C 0.46216(18) 0.6076(6) 0.3384(2) 0.0374(8) Uani 1 1 d . . .
H14 H 0.4460 0.7557 0.3085 0.045 Uiso 1 1 calc R . .
C15 C 0.1535(2) 0.6792(7) 0.2523(3) 0.0469(9) Uani 1 1 d . . .
C16 C 0.1401(2) 0.6095(10) 0.1581(3) 0.0718(14) Uani 1 1 d . . .
H16 H 0.1757 0.5175 0.1423 0.086 Uiso 1 1 calc R . .
C17 C 0.0758(3) 0.6715(13) 0.0873(4) 0.102(2) Uani 1 1 d . . .
H17 H 0.0671 0.6189 0.0231 0.122 Uiso 1 1 calc R . .
C18 C 0.0243(3) 0.8056(13) 0.1064(5) 0.108(2) Uani 1 1 d . . .
H18 H -0.0197 0.8493 0.0560 0.130 Uiso 1 1 calc R . .
C19 C 0.0364(3) 0.8784(10) 0.1996(6) 0.100(2) Uani 1 1 d . . .
H19 H 0.0005 0.9716 0.2143 0.120 Uiso 1 1 calc R . .
C20 C 0.1017(2) 0.8145(7) 0.2725(4) 0.0667(13) Uani 1 1 d . . .
H20 H 0.1102 0.8656 0.3369 0.080 Uiso 1 1 calc R . .
C21 C 0.2026(2) 0.2698(7) 0.4271(3) 0.0511(10) Uani 1 1 d . . .
N22 N 0.1807(2) 0.2165(8) 0.4870(3) 0.0760(12) 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C2 N1 C5 107.6(3) . . ?
N1 C2 C6 122.8(3) . . ?
N1 C2 C3 116.7(3) . . ?
C6 C2 C3 120.5(3) . . ?
C2 C3 C4 102.5(3) . . ?
C2 C3 H3A 111.3 . . ?
C4 C3 H3A 111.3 . . ?
C2 C3 H3B 111.3 . . ?
C4 C3 H3B 111.3 . . ?
H3A C3 H3B 109.2 . . ?
C15 C4 C3 116.5(3) . . ?
C15 C4 C5 113.6(3) . . ?
C3 C4 C5 101.7(3) . . ?
C15 C4 H4 108.2 . . ?
C3 C4 H4 108.2 . . ?
C5 C4 H4 108.2 . . ?
C21 C5 N1 110.8(3) . . ?
C21 C5 C4 112.2(3) . . ?
N1 C5 C4 107.2(3) . . ?
C21 C5 H5 108.8 . . ?
N1 C5 H5 108.8 . . ?
C4 C5 H5 108.8 . . ?
C14 C6 O7 111.5(3) . . ?
C14 C6 C2 130.5(3) . . ?
O7 C6 C2 118.0(3) . . ?
C8 O7 C6 105.5(2) . . ?
O7 C8 C9 125.3(3) . . ?
O7 C8 C13 110.4(3) . . ?
C9 C8 C13 124.3(3) . . ?
C8 C9 C10 115.5(3) . . ?
C8 C9 H9 122.2 . . ?
C10 C9 H9 122.2 . . ?
C9 C10 C11 122.5(3) . . ?
C9 C10 H10 118.8 . . ?
C11 C10 H10 118.8 . . ?
C12 C11 C10 121.2(3) . . ?
C12 C11 H11 119.4 . . ?
C10 C11 H11 119.4 . . ?
C11 C12 C13 117.6(3) . . ?
C11 C12 H12 121.2 . . ?
C13 C12 H12 121.2 . . ?
C8 C13 C12 118.9(3) . . ?
C8 C13 C14 105.4(3) . . ?
C12 C13 C14 135.7(3) . . ?
C6 C14 C13 107.2(3) . . ?
C6 C14 H14 126.4 . . ?
C13 C14 H14 126.4 . . ?
C20 C15 C16 118.4(4) . . ?
C20 C15 C4 121.0(4) . . ?
C16 C15 C4 120.6(4) . . ?
C17 C16 C15 120.5(5) . . ?
C17 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C18 C17 C16 121.6(6) . . ?
C18 C17 H17 119.2 . . ?
C16 C17 H17 119.2 . . ?
C17 C18 C19 119.2(5) . . ?
C17 C18 H18 120.4 . . ?
C19 C18 H18 120.4 . . ?
C18 C19 C20 119.6(5) . . ?
C18 C19 H19 120.2 . . ?
C20 C19 H19 120.2 . . ?
C15 C20 C19 120.7(5) . . ?
C15 C20 H20 119.7 . . ?
C19 C20 H20 119.7 . . ?
N22 C21 C5 179.5(4) . . ?
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
N1 C2 1.271(4) . ?
N1 C5 1.473(5) . ?
C2 C6 1.450(5) . ?
C2 C3 1.503(5) . ?
C3 C4 1.523(5) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C15 1.507(5) . ?
C4 C5 1.563(5) . ?
C4 H4 1.0000 . ?
C5 C21 1.461(5) . ?
C5 H5 1.0000 . ?
C6 C14 1.346(5) . ?
C6 O7 1.378(4) . ?
O7 C8 1.374(4) . ?
C8 C9 1.374(5) . ?
C8 C13 1.393(4) . ?
C9 C10 1.377(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.390(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.383(5) . ?
C11 H11 0.9500 . ?
C12 C13 1.403(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.423(5) . ?
C14 H14 0.9500 . ?
C15 C20 1.366(5) . ?
C15 C16 1.379(6) . ?
C16 C17 1.366(6) . ?
C16 H16 0.9500 . ?
C17 C18 1.348(8) . ?
C17 H17 0.9500 . ?
C18 C19 1.374(8) . ?
C18 H18 0.9500 . ?
C19 C20 1.397(7) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
C21 N22 1.137(5) . ?
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
C5 N1 C2 C6 -176.2(3) . . . . ?
C5 N1 C2 C3 0.8(4) . . . . ?
N1 C2 C3 C4 12.5(4) . . . . ?
C6 C2 C3 C4 -170.5(3) . . . . ?
C2 C3 C4 C15 -142.5(3) . . . . ?
C2 C3 C4 C5 -18.5(3) . . . . ?
C2 N1 C5 C21 -136.4(3) . . . . ?
C2 N1 C5 C4 -13.6(4) . . . . ?
C15 C4 C5 C21 -91.9(4) . . . . ?
C3 C4 C5 C21 142.1(3) . . . . ?
C15 C4 C5 N1 146.2(3) . . . . ?
C3 C4 C5 N1 20.2(4) . . . . ?
N1 C2 C6 C14 173.2(4) . . . . ?
C3 C2 C6 C14 -3.7(5) . . . . ?
N1 C2 C6 O7 -4.0(5) . . . . ?
C3 C2 C6 O7 179.2(3) . . . . ?
C14 C6 O7 C8 -0.2(4) . . . . ?
C2 C6 O7 C8 177.4(3) . . . . ?
C6 O7 C8 C9 179.4(3) . . . . ?
C6 O7 C8 C13 0.0(3) . . . . ?
O7 C8 C9 C10 179.3(3) . . . . ?
C13 C8 C9 C10 -1.4(5) . . . . ?
C8 C9 C10 C11 0.7(5) . . . . ?
C9 C10 C11 C12 -0.1(5) . . . . ?
C10 C11 C12 C13 0.2(5) . . . . ?
O7 C8 C13 C12 -179.1(3) . . . . ?
C9 C8 C13 C12 1.5(5) . . . . ?
O7 C8 C13 C14 0.2(3) . . . . ?
C9 C8 C13 C14 -179.2(3) . . . . ?
C11 C12 C13 C8 -0.8(5) . . . . ?
C11 C12 C13 C14 -179.8(3) . . . . ?
O7 C6 C14 C13 0.3(4) . . . . ?
C2 C6 C14 C13 -177.0(3) . . . . ?
C8 C13 C14 C6 -0.3(4) . . . . ?
C12 C13 C14 C6 178.8(4) . . . . ?
C3 C4 C15 C20 -127.6(4) . . . . ?
C5 C4 C15 C20 114.7(4) . . . . ?
C3 C4 C15 C16 51.6(5) . . . . ?
C5 C4 C15 C16 -66.1(5) . . . . ?
C20 C15 C16 C17 -1.0(7) . . . . ?
C4 C15 C16 C17 179.7(5) . . . . ?
C15 C16 C17 C18 1.3(10) . . . . ?
C16 C17 C18 C19 -1.1(10) . . . . ?
C17 C18 C19 C20 0.6(10) . . . . ?
C16 C15 C20 C19 0.6(7) . . . . ?
C4 C15 C20 C19 179.8(4) . . . . ?
C18 C19 C20 C15 -0.4(8) . . . . ?
N1 C5 C21 N22 38(64) . . . . ?
C4 C5 C21 N22 -82(64) . . . . ?
