#------------------------------------------------------------------------------
#$Date: 2019-03-05 10:52:05 +0200 (Tue, 05 Mar 2019) $
#$Revision: 213973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/03/7150316.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_7150316
loop_
_publ_author_name
'Reisinger, Ales'
'Bernhardt, Paul V.'
'Wentrup, Curt'
_publ_section_title
;
 Synthesis of 1,3-diazepines and ring contraction to cyanopyrroles.
;
_journal_issue                   2
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              246
_journal_page_last               256
_journal_paper_doi               10.1039/b311247k
_journal_volume                  2
_journal_year                    2004
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C6 H7 Cl1 N4 O1'
_chemical_formula_structural     'C6 H7 CL N4 O'
_chemical_formula_sum            'C7 H7 Cl N4 O'
_chemical_formula_weight         198.62
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_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_conform_dict_location     ftp://ftp.iucr.org/cifdics/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.1
_audit_creation_date             2003-08-20T12:19:44-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                105.66(2)
_cell_angle_beta                 94.91(3)
_cell_angle_gamma                102.04(2)
_cell_formula_units_Z            4
_cell_length_a                   7.792(1)
_cell_length_b                   10.213(2)
_cell_length_c                   11.809(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      14.048
_cell_measurement_theta_min      9.787
_cell_measurement_wavelength     0.71073
_cell_volume                     874.9(3)
_computing_cell_refinement       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_collection       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector                 'scintillation LiI'
_diffrn_detector_dtime           1.195
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Enraf Nonius CAD4'
_diffrn_measurement_method       'non-profiled omega scans'
_diffrn_orient_matrix_type
;
x-axis points to radiation source
the matrix is specified in reciprocal space
;
_diffrn_orient_matrix_UB_11      0.75463E-1
_diffrn_orient_matrix_UB_12      0.74551E-1
_diffrn_orient_matrix_UB_13      -0.26687E-1
_diffrn_orient_matrix_UB_21      -0.109091
_diffrn_orient_matrix_UB_22      0.24029E-1
_diffrn_orient_matrix_UB_23      -0.31111E-1
_diffrn_orient_matrix_UB_31      0.5172E-2
_diffrn_orient_matrix_UB_32      0.06959
_diffrn_orient_matrix_UB_33      0.79047E-1
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.038
_diffrn_reflns_av_unetI/netI     0.0821
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            3313
_diffrn_reflns_theta_full        24.98
_diffrn_reflns_theta_max         24.98
_diffrn_reflns_theta_min         1.81
_diffrn_source                   'Enraf Nonius FR590'
_diffrn_standards_decay_%        1
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.399
_exptl_absorpt_correction_T_max  0.9588
_exptl_absorpt_correction_T_min  0.917
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details
;
North A.C.T., Phillips D.C. & Mathews F.S. (1968) Acta. Cryst. A24, 351
Number of psi-scan sets used was   5
Theta correction was applied.
Averaged transmission function was used.
No Fourier smoothing was applied.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.508
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.196
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       0.015(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.979
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         3068
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.979
_refine_ls_R_factor_all          0.1401
_refine_ls_R_factor_gt           0.0438
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0546P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0944
_refine_ls_wR_factor_ref         0.1235
_reflns_number_gt                1429
_reflns_number_total             3068
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b311247k.txt
_cod_data_source_block           cw17298
_cod_database_code               7150316
_exptl_absorpt_factor_mur        0.039
_exptl_absorpt_correction_t_ave  0.9334
_diffrn_standards_decay_corr_max 1.009
_diffrn_standards_decay_corr_min 0.963
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
N1 N 0.1817(4) 0.4136(3) 0.8017(3) 0.0580(8) Uani 1 1 d . . .
N2 N 0.1193(4) 0.5171(3) 0.7763(3) 0.0628(9) Uani 1 1 d . . .
N3 N 0.0825(4) 0.4980(3) 0.6620(3) 0.0639(9) Uani 1 1 d . . .
N4 N 0.1261(4) 0.3753(3) 0.6100(3) 0.0504(8) Uani 1 1 d . . .
O1 O 0.2947(3) 0.1514(2) 0.7520(2) 0.0604(7) Uani 1 1 d . . .
Cl1 Cl 0.15313(17) 0.10715(12) 0.31013(8) 0.0825(4) Uani 1 1 d . . .
C5 C 0.1110(5) 0.3136(4) 0.4897(3) 0.0569(10) Uani 1 1 d . . .
H5 H 0.0688 0.3524 0.4335 0.068 Uiso 1 1 calc R . .
C6 C 0.1622(5) 0.1922(4) 0.4596(3) 0.0541(10) Uani 1 1 d . . .
C7 C 0.2251(5) 0.1310(4) 0.5429(3) 0.0533(10) Uani 1 1 d . . .
H7 H 0.2583 0.0467 0.5175 0.064 Uiso 1 1 calc R . .
C8 C 0.2367(5) 0.1961(4) 0.6610(3) 0.0518(10) Uani 1 1 d . . .
C8A C 0.1850(5) 0.3243(4) 0.6963(3) 0.0455(9) Uani 1 1 d . . .
C9 C 0.3437(6) 0.0187(4) 0.7190(3) 0.0647(11) Uani 1 1 d . . .
H9A H 0.4452 0.0256 0.677 0.078 Uiso 1 1 calc R . .
H9B H 0.2458 -0.0537 0.6676 0.078 Uiso 1 1 calc R . .
C10 C 0.3887(6) -0.0157(5) 0.8319(4) 0.0847(14) Uani 1 1 d . . .
H10A H 0.4866 0.0562 0.8816 0.127 Uiso 1 1 calc R . .
H10B H 0.4206 -0.1041 0.8134 0.127 Uiso 1 1 calc R . .
H10C H 0.2876 -0.0212 0.8731 0.127 Uiso 1 1 calc R . .
N1' N -0.2936(4) 0.2161(3) 0.5819(3) 0.0577(9) Uani 1 1 d . . .
N2' N -0.3435(4) 0.2541(3) 0.4854(3) 0.0655(9) Uani 1 1 d . . .
N3' N -0.3913(4) 0.3721(3) 0.5139(3) 0.0640(9) Uani 1 1 d . . .
N4' N -0.3711(4) 0.4147(3) 0.6353(2) 0.0488(8) Uani 1 1 d . . .
C5' C -0.4021(5) 0.5349(4) 0.7062(3) 0.0552(10) Uani 1 1 d . . .
H5' H -0.4437 0.5988 0.6748 0.066 Uiso 1 1 calc R . .
C6' C -0.3690(5) 0.5549(4) 0.8237(3) 0.0533(10) Uani 1 1 d . . .
C7' C -0.3061(5) 0.4596(4) 0.8731(3) 0.0542(10) Uani 1 1 d . . .
H7' H -0.2851 0.4779 0.9552 0.065 Uiso 1 1 calc R . .
C8' C -0.2762(5) 0.3403(4) 0.8000(3) 0.0509(10) Uani 1 1 d . . .
C8A' C -0.3103(5) 0.3180(4) 0.6754(3) 0.0466(9) Uani 1 1 d . . .
C9' C -0.1457(5) 0.2694(4) 0.9559(3) 0.0619(11) Uani 1 1 d . . .
H9'1 H -0.2418 0.2751 1.0026 0.074 Uiso 1 1 calc R . .
H9'2 H -0.057 0.3577 0.9842 0.074 Uiso 1 1 calc R . .
C10' C -0.0662(6) 0.1527(5) 0.9672(3) 0.0724(12) Uani 1 1 d . . .
H10D H -0.1551 0.0659 0.9389 0.109 Uiso 1 1 calc R . .
H10E H -0.021 0.1684 1.0492 0.109 Uiso 1 1 calc R . .
H10F H 0.029 0.1484 0.9209 0.109 Uiso 1 1 calc R . .
O1' O -0.2117(3) 0.2406(2) 0.8314(2) 0.0594(7) Uani 1 1 d . . .
Cl1' Cl -0.40665(15) 0.70242(11) 0.91993(9) 0.0752(4) 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 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_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
-4 -2 2
0 5 -5
-1 1 5
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
C8A N1 N2 105.2(3) . . ?
N3 N2 N1 113.0(3) . . ?
N2 N3 N4 104.6(3) . . ?
C8A N4 N3 108.7(3) . . ?
C8A N4 C5 125.8(3) . . ?
N3 N4 C5 125.5(3) . . ?
C8 O1 C9 116.1(3) . . ?
C6 C5 N4 114.6(3) . . ?
C5 C6 C7 123.7(3) . . ?
C5 C6 Cl1 118.5(3) . . ?
C7 C6 Cl1 117.8(3) . . ?
C8 C7 C6 119.4(3) . . ?
O1 C8 C7 126.6(3) . . ?
O1 C8 C8A 114.7(3) . . ?
C7 C8 C8A 118.7(3) . . ?
N1 C8A N4 108.4(3) . . ?
N1 C8A C8 133.7(3) . . ?
N4 C8A C8 117.9(3) . . ?
O1 C9 C10 107.1(3) . . ?
C8A' N1' N2' 105.5(3) . . ?
N3' N2' N1' 112.3(3) . . ?
N2' N3' N4' 105.6(3) . . ?
C8A' N4' N3' 108.1(3) . . ?
C8A' N4' C5' 124.9(3) . . ?
N3' N4' C5' 127.0(3) . . ?
C6' C5' N4' 115.8(3) . . ?
C5' C6' C7' 123.0(3) . . ?
C5' C6' Cl1' 119.1(3) . . ?
C7' C6' Cl1' 117.8(3) . . ?
C8' C7' C6' 119.9(3) . . ?
O1' C8' C7' 127.9(3) . . ?
O1' C8' C8A' 114.4(3) . . ?
C7' C8' C8A' 117.6(3) . . ?
N1' C8A' N4' 108.5(3) . . ?
N1' C8A' C8' 132.8(3) . . ?
N4' C8A' C8' 118.7(3) . . ?
O1' C9' C10' 107.2(3) . . ?
C8' O1' C9' 116.8(3) . . ?
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 C8A 1.336(4) . ?
N1 N2 1.342(4) . ?
N2 N3 1.309(4) . ?
N3 N4 1.364(4) . ?
N4 C8A 1.351(4) . ?
N4 C5 1.374(4) . ?
O1 C8 1.355(4) . ?
O1 C9 1.445(4) . ?
Cl1 C6 1.732(3) . ?
C5 C6 1.347(5) . ?
C6 C7 1.406(5) . ?
C7 C8 1.359(4) . ?
C8 C8A 1.416(5) . ?
C9 C10 1.500(5) . ?
N1' C8A' 1.335(4) . ?
N1' N2' 1.351(4) . ?
N2' N3' 1.301(4) . ?
N3' N4' 1.365(4) . ?
N4' C8A' 1.355(4) . ?
N4' C5' 1.368(4) . ?
C5' C6' 1.341(5) . ?
C6' C7' 1.408(5) . ?
C6' Cl1' 1.722(4) . ?
C7' C8' 1.368(5) . ?
C8' O1' 1.345(4) . ?
C8' C8A' 1.419(4) . ?
C9' O1' 1.445(4) . ?
C9' C10' 1.483(5) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 10186223
