#------------------------------------------------------------------------------
#$Date: 2018-06-14 15:53:24 +0300 (Thu, 14 Jun 2018) $
#$Revision: 208377 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/00/37/2003707.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2003707
loop_
_publ_author_name
'Bachechi, F.'
'Gavuzzo, E.'
'Cerreto, F.'
'Scalzo, M.'
_publ_section_title
;
 A 1,5-Diarylpyrrole Derivative
;
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1431
_journal_page_last               1434
_journal_paper_doi               10.1107/S0108270195000734
_journal_volume                  51
_journal_year                    1995
_chemical_formula_moiety         'C20 H16 Cl3 N1 O2'
_chemical_formula_sum            'C20 H16 Cl3 N O2'
_chemical_formula_weight         408.71
_chemical_name_systematic
; 1-(2,4-dichlorophenyl)-5-(4-chlorophenyl)-3-etoxycarbonyl-
 2-methyl-pyrrole
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_cell_angle_alpha                90.00
_cell_angle_beta                 92.37(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.504(2)
_cell_length_b                   13.121(2)
_cell_length_c                   22.192(2)
_cell_measurement_reflns_used    15
_cell_measurement_temperature    295
_cell_measurement_theta_max      40.0
_cell_measurement_theta_min      39.0
_cell_volume                     1892.2(7)
_computing_cell_refinement       'MSC/AFC Diffractometer Control Software'
_computing_data_collection
;
MSC/AFC Diffractometer Control Software (Molecular
Structure Corporation, 1988)
;
_computing_data_reduction
;
TEXSAN (Molecular Structure Corporation, 1985)
;
_computing_molecular_graphics    TEXSAN
_computing_structure_refinement  TEXSAN
_computing_structure_solution
;
TEXSAN (Molecular Structure Corporation, 1985)
;
_diffrn_ambient_temperature      298
_diffrn_measurement_device       'Rigaku AFC5R'
_diffrn_measurement_method       'profile data from ω-2θ'
_diffrn_radiation_monochromator  'equatorial mounted graphite'
_diffrn_radiation_source
;
Rigaku AFC5R diffractometer on a 12KW Rotating Anode Generator
;
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.027
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            3046
_diffrn_reflns_theta_max         62.0
_diffrn_reflns_theta_min         2.5
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    4.594
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.78
_exptl_absorpt_correction_type   'empirical via \y scan at \c = 90\%'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_description       prism
_exptl_crystal_F_000             840.0
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.45
_refine_diff_density_min         -1.65
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_obs   2.36
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         1955
_refine_ls_R_factor_obs          0.048
_refine_ls_shift/esd_max         0.69
_refine_ls_structure_factor_coef F
_refine_ls_weighting_scheme      'sigma with w = 1/[\s^2^(F)]'
_refine_ls_wR_factor_obs         0.064
_reflns_number_observed          1955
_reflns_number_total             3046
_reflns_observed_criterion       >3\s(I)
_cod_data_source_file            na1117.cif
_cod_data_source_block           Bachechi
_cod_depositor_comments
;
 Updating space group information and adding the symmetry operation list.

 Antanas Vaitkus,
 2018-06-15
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_original_formula_sum        'C20 H16 Cl3 N1 O2'
_cod_database_code               2003707
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y+1/2,z+1/2
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_B_iso_or_equiv
Cl1 0.8185(2) 0.7468(1) 0.02791(5) 6.94(7)
Cl2 0.1788(2) 0.4999(1) 0.06449(5) 5.75(6)
Cl3 0.8160(2) 0.0747(1) 0.03820(6) 7.45(8)
O1 -0.0855(5) 0.3567(2) 0.3204(1) 5.9(2)
O2 -0.0912(5) 0.5267(2) 0.3161(1) 6.4(2)
N1 0.3676(5) 0.4742(2) 0.1888(1) 3.4(1)
C2 0.2362(6) 0.5142(3) 0.2296(2) 3.6(2)
C3 0.1256(6) 0.4347(3) 0.2521(2) 3.7(2)
C4 0.1912(6) 0.3443(3) 0.2241(2) 3.9(2)
C5 0.3387(6) 0.3681(3) 0.1850(2) 3.5(2)
C6 0.4796(6) 0.5367(3) 0.1487(2) 3.4(2)
C7 0.6583(6) 0.5844(3) 0.1691(2) 4.1(2)
C8 0.7634(6) 0.6487(3) 0.1322(2) 4.6(2)
C9 0.6896(7) 0.6641(3) 0.0744(2) 4.3(2)
C10 0.5117(7) 0.6183(3) 0.0526(2) 4.2(2)
C11 0.4064(6) 0.5546(3) 0.0902(2) 3.6(2)
C12 0.2350(7) 0.6255(3) 0.2440(2) 4.7(2)
C13 -0.0240(6) 0.4464(3) 0.2982(2) 4.5(2)
C14 -0.2305(8) 0.3602(4) 0.3710(2) 6.2(3)
C15 -0.4353(9) 0.3763(4) 0.3442(3) 7.4(3)
C17 0.4594(6) 0.3008(3) 0.1467(2) 3.5(2)
C18 0.6597(6) 0.3203(3) 0.1313(2) 4.4(2)
C19 0.7694(7) 0.2522(3) 0.0974(2) 4.9(2)
C20 0.6790(7) 0.1623(3) 0.0795(2) 4.6(2)
C21 0.4812(7) 0.1398(3) 0.0942(2) 4.8(2)
C22 0.3726(6) 0.2085(3) 0.1277(2) 4.2(2)
H1 0.140272 0.277771 0.231478 ?
H2 0.236027 0.192515 0.137969 ?
H3 0.419480 0.077412 0.081540 ?
H4 0.905884 0.267585 0.086719 ?
H5 0.723583 0.382023 0.144279 ?
H6 0.709545 0.572779 0.209185 ?
H7 0.885455 0.681820 0.146773 ?
H8 0.461782 0.630153 0.012387 ?
H9 -0.225596 0.297744 0.392662 ?
H10 -0.194607 0.414710 0.397654 ?
H11 -0.438419 0.438672 0.322412 ?
H12 -0.469537 0.321695 0.317508 ?
H13 -0.532080 0.379077 0.375063 ?
H14 0.367247 0.645441 0.259519 ?
H15 0.201216 0.663151 0.208376 ?
H16 0.135684 0.638706 0.273230 ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_source
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
C Carbon 'International Tables Vol IV Tables 2.2A, 2.2C, 2.3.1' .002 .002
O Oxygen 'International Tables Vol IV Tables 2.2A, 2.2C, 2.3.1' .008 .006
H Hydrogen 'International Tables Vol IV Tables 2.2A, 2.2C, 2.3.1' .000 .000
N Nitrogen 'International Tables Vol IV Tables 2.2A, 2.2C, 2.3.1' .004 .003
Cl Chlorine 'International Tables Vol IV Tables 2.2A, 2.2C, 2.3.1' .132 .159
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
1 0 -1
-1 -1 2
0 1 3
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C13 O1 C14 117.1(3) yes
C2 N1 C5 109.4(3) yes
C2 N1 C6 122.5(3) yes
C5 N1 C6 126.8(3) yes
N1 C2 C3 107.3(3) yes
N1 C2 C12 121.5(3) yes
C3 C2 C12 131.1(3) yes
C2 C3 C4 107.8(3) yes
C2 C3 C13 123.6(3) yes
C4 C3 C13 128.5(3) yes
C3 C4 C5 108.8(3) yes
N1 C5 C4 106.6(3) yes
N1 C5 C17 123.6(3) yes
C4 C5 C17 129.7(3) yes
N1 C6 C7 119.9(3) yes
N1 C6 C11 121.1(3) yes
C7 C6 C11 118.9(3) yes
C6 C7 C8 121.1(3) yes
C7 C8 C9 119.0(4) yes
Cl1 C9 C8 119.4(3) yes
Cl1 C9 C10 119.0(3) yes
C8 C9 C10 121.6(4) yes
C9 C10 C11 118.9(3) yes
Cl2 C11 C6 119.9(3) yes
Cl2 C11 C10 119.5(3) yes
C6 C11 C10 120.6(4) yes
O1 C14 C15 107.0(4) yes
O1 C13 O2 121.5(4) yes
O1 C13 C3 112.7(3) yes
O2 C13 C3 125.8(4) yes
C5 C17 C18 124.1(3) yes
C5 C17 C22 118.4(3) yes
C18 C17 C22 117.3(3) yes
C17 C18 C19 121.8(4) yes
C18 C19 C20 119.3(4) yes
Cl3 C20 C19 119.9(4) yes
Cl3 C20 C21 119.3(3) yes
C19 C20 C21 120.7(4) yes
C20 C21 C22 119.6(4) yes
C17 C22 C21 121.3(4) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C9 1.736(4) yes
Cl2 C11 1.721(4) yes
Cl3 C20 1.739(4) yes
O1 C14 1.497(5) yes
O1 C13 1.344(5) yes
O2 C13 1.213(5) yes
N1 C2 1.375(5) yes
N1 C5 1.407(4) yes
N1 C6 1.432(4) yes
C2 C3 1.372(5) yes
C2 C12 1.495(5) yes
C3 C4 1.413(5) yes
C3 C13 1.449(5) yes
C4 C5 1.356(5) yes
C5 C17 1.475(5) yes
C6 C7 1.380(5) yes
C6 C11 1.383(5) yes
C7 C8 1.375(5) yes
C8 C9 1.367(5) yes
C9 C10 1.374(6) yes
C10 C11 1.383(5) yes
C14 C15 1.452(7) yes
C17 C18 1.384(5) yes
C17 C22 1.394(5) yes
C18 C19 1.385(5) yes
C19 C20 1.369(6) yes
C20 C21 1.373(6) yes
C21 C22 1.380(5) yes
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
C2 N1 C6 C7 80.6(5)
N1 C5 C17 C18 28.9(6)
