#------------------------------------------------------------------------------
#$Date: 2016-02-20 02:53:41 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176768 $
#$URL: svn://www.crystallography.net/cod/cif/2/10/14/2101448.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_2101448
loop_
_publ_author_name
'Böcskei, Zs.'
'Simon, K.'
'Németh, V.'
'Ágai, B.'
'Toke, L.'
_publ_section_title
;
 Interesting conformational and substitutional disorder in the crystal
 structures of three homologous crowns
;
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              194
_journal_page_last               200
_journal_paper_doi               10.1107/S0108768195008135
_journal_volume                  52
_journal_year                    1996
_chemical_formula_sum            'C16 H16 Cl N O3'
_chemical_formula_weight         305.75
_chemical_name_systematic
;
 ?
;
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_space_group_name_H-M   'P 1 21/a 1'
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 93.04(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   13.922(6)
_cell_length_b                   6.951(3)
_cell_length_c                   30.173(7)
_cell_measurement_temperature    298(2)
_cell_volume                     2915.8(19)
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.0985
_diffrn_reflns_av_sigmaI/netI    0.3320
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            4542
_diffrn_reflns_theta_max         60.00
_diffrn_reflns_theta_min         2.93
_exptl_absorpt_coefficient_mu    2.407
_exptl_crystal_density_diffrn    1.393
_exptl_crystal_F_000             1280
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.08
_refine_diff_density_max         1.079
_refine_diff_density_min         -0.363
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   0.970
_refine_ls_goodness_of_fit_obs   1.308
_refine_ls_matrix_type           full
_refine_ls_number_parameters     375
_refine_ls_number_reflns         4187
_refine_ls_number_restraints     50
_refine_ls_restrained_S_all      1.058
_refine_ls_restrained_S_obs      1.274
_refine_ls_R_factor_all          0.3347
_refine_ls_R_factor_obs          0.0748
_refine_ls_shift/esd_max         0.002
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1345P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.3420
_refine_ls_wR_factor_obs         0.1907
_reflns_number_observed          1110
_reflns_number_total             4323
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            ka0027.cif
_cod_data_source_block           nai
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.1345P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.1345P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        2916.(2)
_cod_original_sg_symbol_H-M      'P 21/a'
_cod_database_code               2101448
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_type_symbol
Cl1 0.3414(3) -0.4028(5) 1.33051(12) 0.0761(12) Uani d . 1 Cl
C2 0.2560(7) -0.2212(15) 1.3268(4) 0.046(3) Uani d D 1 C
C3 0.2431(8) -0.0979(15) 1.3619(3) 0.047(3) Uani d D 1 C
H3 0.2823(8) -0.1109(15) 1.3876(3) 0.052(9) Uiso calc R 1 H
C4 0.1741(7) 0.0427(16) 1.3598(3) 0.049(4) Uani d D 1 C
C5 0.1147(8) 0.0518(16) 1.3209(3) 0.048(3) Uani d D 1 C
C6 0.1286(8) -0.0704(17) 1.2850(3) 0.053(4) Uani d D 1 C
H6 0.0892(8) -0.0606(17) 1.2592(3) 0.052(9) Uiso calc R 1 H
C7 0.2008(8) -0.2046(17) 1.2880(3) 0.050(4) Uani d D 1 C
H7 0.2122(8) -0.2836(17) 1.2639(3) 0.052(9) Uiso calc R 1 H
N8 0.1537(6) 0.1676(12) 1.3934(2) 0.052(3) Uani d D 1 N
H8 0.0941(6) 0.1791(12) 1.3991(2) 0.052(9) Uiso calc R 1 H
C9 0.2200(6) 0.2798(13) 1.4199(3) 0.044(3) Uani d D 1 C
C10 0.3196(6) 0.2665(16) 1.4175(3) 0.053(4) Uani d D 1 C
H10 0.3460(6) 0.1767(16) 1.3988(3) 0.052(9) Uiso calc R 1 H
C11 0.3789(8) 0.3877(18) 1.4430(4) 0.063(4) Uani d D 1 C
H11 0.4451(8) 0.3848(18) 1.4402(4) 0.052(9) Uiso calc R 1 H
C12 0.3405(8) 0.5110(18) 1.4723(4) 0.067(4) Uani d D 1 C
H12 0.3815(8) 0.5871(18) 1.4901(4) 0.052(9) Uiso calc R 1 H
C13 0.2430(8) 0.5267(17) 1.4762(3) 0.059(4) Uani d D 1 C
H13 0.2177(8) 0.6146(17) 1.4957(3) 0.052(9) Uiso calc R 1 H
C14 0.1844(7) 0.4088(16) 1.4505(3) 0.044(3) Uani d D 1 C
O15 0.0833(5) 0.4067(12) 1.4527(2) 0.057(2) Uani d D 1 O
C16 0.0353(8) 0.5844(18) 1.4427(3) 0.063(4) Uani d D 1 C
H16A 0.0666(8) 0.6863(18) 1.4600(3) 0.044(8) Uiso calc R 1 H
H16B -0.0306(8) 0.5755(18) 1.4513(3) 0.044(8) Uiso calc R 1 H
C17 0.0355(9) 0.6344(16) 1.3954(3) 0.060(4) Uani d D 1 C
H17A 0.0063(9) 0.7597(16) 1.3904(3) 0.044(8) Uiso calc R 1 H
H17B 0.1010(9) 0.6394(16) 1.3861(3) 0.044(8) Uiso calc R 1 H
O18 -0.0175(5) 0.4921(12) 1.3707(2) 0.055(2) Uani d D 1 O
C19 -0.0110(8) 0.4990(16) 1.3240(3) 0.057(4) Uani d D 1 C
H19A 0.0008(8) 0.6308(16) 1.3153(3) 0.044(8) Uiso calc R 1 H
H19B -0.0723(8) 0.4602(16) 1.3101(3) 0.044(8) Uiso calc R 1 H
C20 0.0650(8) 0.3758(16) 1.3072(4) 0.062(4) Uani d D 1 C
H20A 0.0691(8) 0.3930(16) 1.2755(4) 0.044(8) Uiso calc R 1 H
H20B 0.1268(8) 0.4076(16) 1.3217(4) 0.044(8) Uiso calc R 1 H
O21 0.0386(5) 0.1795(11) 1.3172(2) 0.052(2) Uani d D 1 O
Cl1' 0.4706(3) 0.2414(5) 0.99251(11) 0.0769(13) Uani d . 1 Cl
C2' 0.4716(8) 0.8998(17) 1.1264(4) 0.062(4) Uani d D 1 C
H2' 0.5029(8) 0.9812(17) 1.1074(4) 0.052(9) Uiso calc R 1 H
C3' 0.4034(8) 0.7720(16) 1.1093(3) 0.053(4) Uani d D 1 C
H3' 0.3893(8) 0.7699(16) 1.0789(3) 0.052(9) Uiso calc R 1 H
C4' 0.3560(8) 0.6488(16) 1.1356(3) 0.047(3) Uani d D 1 C
C5' 0.3764(8) 0.6607(16) 1.1815(3) 0.055(4) Uani d D 1 C
C6' 0.4453(8) 0.7895(17) 1.1990(3) 0.056(4) Uani d D 1 C
H6' 0.4587(8) 0.7954(17) 1.2295(3) 0.052(9) Uiso calc R 1 H
C7' 0.4934(8) 0.9073(17) 1.1712(4) 0.068(4) Uani d D 1 C
H7' 0.5403(8) 0.9914(17) 1.1827(4) 0.052(9) Uiso calc R 1 H
N8' 0.2859(4) 0.5181(8) 1.1214(2) 0.053(3) Uani d D 1 N
H8' 0.2326(4) 0.5201(8) 1.1345(2) 0.052(9) Uiso calc R 1 H
C9' 0.2944(4) 0.3813(8) 1.0870(2) 0.046(3) Uani d RD 1 C
C10' 0.3731(4) 0.3760(8) 1.0598(2) 0.045(3) Uani d RD 1 C
H10' 0.4241(4) 0.4611(8) 1.0646(2) 0.052(9) Uiso calc R 1 H
C11' 0.3735(8) 0.2429(17) 1.0260(3) 0.051(4) Uani d D 1 C
C12' 0.3017(9) 0.1120(18) 1.0196(3) 0.059(4) Uani d D 1 C
H12' 0.3053(9) 0.0209(18) 0.9972(3) 0.052(9) Uiso calc R 1 H
C13' 0.2237(8) 0.1116(16) 1.0458(3) 0.054(4) Uani d D 1 C
H13' 0.1739(8) 0.0236(16) 1.0412(3) 0.052(9) Uiso calc R 1 H
C14' 0.2221(7) 0.2455(15) 1.0790(3) 0.044(3) Uani d D 1 C
O15' 0.1447(5) 0.2594(12) 1.1077(2) 0.060(2) Uani d D 1 O
C16' 0.1297(8) 0.0922(18) 1.1340(3) 0.064(4) Uani d D 1 C
H16C 0.1283(8) -0.0204(18) 1.1150(3) 0.044(8) Uiso calc R 1 H
H16D 0.0676(8) 0.1021(18) 1.1470(3) 0.044(8) Uiso calc R 1 H
C17' 0.2042(8) 0.0663(16) 1.1695(3) 0.060(4) Uani d D 1 C
H17C 0.1939(8) -0.0541(16) 1.1848(3) 0.044(8) Uiso calc R 1 H
H17D 0.2669(8) 0.0612(16) 1.1570(3) 0.044(8) Uiso calc R 1 H
O18' 0.2012(5) 0.2217(12) 1.2000(3) 0.065(3) Uani d D 1 O
C19' 0.2818(7) 0.2378(16) 1.2306(3) 0.058(4) Uani d D 1 C
H19C 0.3051(7) 0.1097(16) 1.2380(3) 0.044(8) Uiso calc R 1 H
H19D 0.2612(7) 0.2966(16) 1.2576(3) 0.044(8) Uiso calc R 1 H
C20' 0.3616(8) 0.3507(16) 1.2143(4) 0.060(4) Uani d D 1 C
H20C 0.4171(8) 0.3436(16) 1.2350(4) 0.044(8) Uiso calc R 1 H
H20D 0.3796(8) 0.3025(16) 1.1858(4) 0.044(8) Uiso calc R 1 H
O21' 0.3273(6) 0.5476(12) 1.2102(2) 0.062(3) Uani d D 1 O
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0181 0.0091 '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
C7 C2 C3 120.9(9)
C7 C2 Cl1 117.9(8)
C3 C2 Cl1 121.2(8)
C4 C3 C2 121.8(8)
C3 C4 N8 126.1(8)
C3 C4 C5 116.9(9)
N8 C4 C5 116.9(9)
O21 C5 C6 117.6(8)
O21 C5 C4 120.9(9)
C6 C5 C4 121.5(9)
C7 C6 C5 119.6(9)
C2 C7 C6 119.3(9)
C4 N8 C9 127.4(7)
C10 C9 C14 117.7(6)
C10 C9 N8 123.5(6)
C14 C9 N8 118.7(7)
C11 C10 C9 119.7(7)
C12 C11 C10 120.1(9)
C11 C12 C13 122.1(9)
C14 C13 C12 117.8(9)
C13 C14 C9 122.5(8)
C13 C14 O15 123.0(9)
C9 C14 O15 114.5(8)
C14 O15 C16 115.9(8)
O15 C16 C17 112.7(9)
O18 C17 C16 108.5(9)
C19 O18 C17 116.1(8)
O18 C19 C20 114.0(8)
O21 C20 C19 106.4(8)
C5 O21 C20 114.9(8)
C7' C2' C3' 120.2(9)
C4' C3' C2' 122.3(9)
C3' C4' N8' 126.0(8)
C3' C4' C5' 117.3(9)
N8' C4' C5' 116.6(8)
O21' C5' C6' 118.7(9)
O21' C5' C4' 120.4(9)
C6' C5' C4' 120.8(9)
C7' C6' C5' 119.9(9)
C6' C7' C2' 119.4(9)
C4' N8' C9' 125.6(5)
C14' C9' C10' 117.5(4)
C14' C9' N8' 119.6(4)
C10' C9' N8' 123.0
C11' C10' C9' 119.0(5)
C12' C11' C10' 121.4(8)
C12' C11' Cl1' 120.4(8)
C10' C11' Cl1' 118.1(8)
C11' C12' C13' 121.2(9)
C14' C13' C12' 117.6(9)
C13' C14' C9' 123.2(8)
C13' C14' O15' 122.3(9)
C9' C14' O15' 114.4(8)
C14' O15' C16' 114.9(8)
O15' C16' C17' 112.8(9)
O18' C17' C16' 109.7(9)
C19' O18' C17' 115.6(8)
O18' C19' C20' 114.3(8)
O21' C20' C19' 106.4(8)
C5' O21' C20' 114.8(8)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C2 1.733(10)
C2 C7 1.371(12)
C2 C3 1.381(11)
C3 C4 1.369(11)
C4 N8 1.376(10)
C4 C5 1.401(11)
C5 O21 1.382(10)
C5 C6 1.399(12)
C6 C7 1.371(12)
N8 C9 1.420(7)
C9 C10 1.395(7)
C9 C14 1.398(10)
C10 C11 1.386(11)
C11 C12 1.359(12)
C12 C13 1.373(12)
C13 C14 1.368(12)
C14 O15 1.413(9)
O15 C16 1.429(11)
C16 C17 1.467(12)
C17 O18 1.421(10)
O18 C19 1.418(10)
C19 C20 1.471(11)
C20 O21 1.448(11)
Cl1' C11' 1.728(10)
C2' C7' 1.372(12)
C2' C3' 1.380(12)
C3' C4' 1.360(11)
C4' N8' 1.385(10)
C4' C5' 1.401(11)
C5' O21' 1.379(10)
C5' C6' 1.395(12)
C6' C7' 1.372(12)
N8' C9' 1.42
C9' C14' 1.392(10)
C9' C10' 1.40
C10' C11' 1.379(11)
C11' C12' 1.358(12)
C12' C13' 1.377(12)
C13' C14' 1.367(11)
C14' O15' 1.420(9)
O15' C16' 1.429(11)
C16' C17' 1.462(12)
C17' O18' 1.422(11)
O18' C19' 1.418(10)
C19' C20' 1.465(11)
C20' O21' 1.452(11)
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
C7 C2 C3 C4 1.2(18)
Cl1 C2 C3 C4 -178.1(9)
C2 C3 C4 N8 177.7(11)
C2 C3 C4 C5 2.2(17)
C3 C4 C5 O21 175.2(10)
N8 C4 C5 O21 -0.7(16)
C3 C4 C5 C6 -3.4(17)
N8 C4 C5 C6 -179.3(10)
O21 C5 C6 C7 -177.4(10)
C4 C5 C6 C7 1.2(18)
C3 C2 C7 C6 -3.4(18)
Cl1 C2 C7 C6 175.9(9)
C5 C6 C7 C2 2.2(18)
C3 C4 N8 C9 48.7(17)
C5 C4 N8 C9 -135.8(11)
C4 N8 C9 C10 -5.4(17)
C4 N8 C9 C14 175.6(10)
C14 C9 C10 C11 -3.9(17)
N8 C9 C10 C11 177.1(10)
C9 C10 C11 C12 3.9(18)
C10 C11 C12 C13 -3.(2)
C11 C12 C13 C14 2.(2)
C12 C13 C14 C9 -2.1(18)
C12 C13 C14 O15 177.7(11)
C10 C9 C14 C13 3.1(17)
N8 C9 C14 C13 -177.8(11)
C10 C9 C14 O15 -176.7(10)
N8 C9 C14 O15 2.4(14)
C13 C14 O15 C16 59.9(13)
C9 C14 O15 C16 -120.2(10)
C14 O15 C16 C17 71.1(11)
O15 C16 C17 O18 63.6(12)
C16 C17 O18 C19 -169.5(9)
C17 O18 C19 C20 93.1(11)
O18 C19 C20 O21 64.1(12)
C6 C5 O21 C20 -102.2(11)
C4 C5 O21 C20 79.2(13)
C19 C20 O21 C5 -155.0(8)
C7' C2' C3' C4' -0.5(19)
C2' C3' C4' N8' 179.1(11)
C2' C3' C4' C5' 2.3(18)
C3' C4' C5' O21' 176.5(10)
N8' C4' C5' O21' -0.6(16)
C3' C4' C5' C6' -2.3(18)
N8' C4' C5' C6' -179.4(10)
O21' C5' C6' C7' -178.3(11)
C4' C5' C6' C7' 0.5(19)
C5' C6' C7' C2' 1.3(19)
C3' C2' C7' C6' -1.(2)
C3' C4' N8' C9' 51.7(14)
C5' C4' N8' C9' -131.6(8)
C4' N8' C9' C14' 173.6(9)
C4' N8' C9' C10' -6.9(6)
C14' C9' C10' C11' 2.2(7)
N8' C9' C10' C11' -177.3(6)
C9' C10' C11' C12' -2.9(13)
C9' C10' C11' Cl1' 179.2(4)
C10' C11' C12' C13' 2.5(19)
Cl1' C11' C12' C13' -179.7(10)
C11' C12' C13' C14' -1.3(19)
C12' C13' C14' C9' 0.6(17)
C12' C13' C14' O15' 179.4(10)
C10' C9' C14' C13' -1.1(12)
N8' C9' C14' C13' 178.4(8)
C10' C9' C14' O15' -180.0(5)
N8' C9' C14' O15' -0.4(9)
C13' C14' O15' C16' 61.6(13)
C9' C14' O15' C16' -119.5(9)
C14' O15' C16' C17' 72.2(11)
O15' C16' C17' O18' 64.1(12)
C16' C17' O18' C19' -166.9(9)
C17' O18' C19' C20' 87.5(12)
O18' C19' C20' O21' 67.0(12)
C6' C5' O21' C20' -101.2(12)
C4' C5' O21' C20' 80.0(14)
C19' C20' O21' C5' -158.0(8)
