#------------------------------------------------------------------------------
#$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/96/2009638.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_2009638
loop_
_publ_author_name
'Sabatino, P.'
'Recanatini, M.'
'Tumiatti, V.'
'Melchiorre, C.'
_publ_section_title
;
 Structural studies on the antimuscarinic agents spiro-DAMP and
 hydroxy-DAMP, and comparison with related compounds
;
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              640
_journal_page_last               645
_journal_paper_doi               10.1107/S0108270193010017
_journal_volume                  50
_journal_year                    1994
_chemical_formula_moiety         'C21 H26 N1 O3 1+ , I1 1-'
_chemical_formula_sum            'C21 H26 I N O3'
_chemical_formula_weight         467.3
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_space_group_name_H-M   'P 1 21/a 1'
_atom_type_scat_source           IntTabIV
_cell_angle_alpha                90.
_cell_angle_beta                 113.9(2)
_cell_angle_gamma                90.
_cell_formula_units_Z            4
_cell_length_a                   9.681(2)
_cell_length_b                   22.465(6)
_cell_length_c                   10.463(5)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293
_cell_measurement_theta_max      11
_cell_measurement_theta_min      7
_cell_volume                     2080(3)
_diffrn_measurement_device       'Enraf-Nonius CAD-4'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.01
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3029
_diffrn_reflns_theta_max         25
_diffrn_standards_decay_%        none
_diffrn_standards_interval_time  160
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    1.54
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'transparent yellow'
_exptl_crystal_density_diffrn    1.49
_exptl_crystal_description       plate
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.5
_refine_diff_density_min         0.45
_refine_ls_goodness_of_fit_obs   1.5
_refine_ls_hydrogen_treatment    'H atoms refined as riding models'
_refine_ls_number_parameters     188
_refine_ls_number_reflns         1556
_refine_ls_R_factor_obs          0.043
_refine_ls_shift/esd_max         0.07
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 1.1/[σ²(Fₒ) + 0.0004(Fₒ)²]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_obs         0.046
_reflns_number_observed          1556
_reflns_number_total             2884
_reflns_observed_criterion       I>2\s(I)
_cod_data_source_file            na1044.cif
_cod_data_source_block           na1044b
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value '1.1/[\s^2^(F~o~) +
0.0004(F~o~)^2^]' was changed to 'calc'. New tag
'_refine_ls_weighting_details' was created. The value of the new tag
was set to 'w = 1.1/[\s^2^(F~o~) + 0.0004(F~o~)^2^]'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        2080.0(10)
_cod_original_sg_symbol_H-M      'P 21/a'
_cod_original_formula_sum        'C21 H26 I1 N1 O3'
_cod_database_code               2009638
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
I .21210(8) .09557(4) .90892(8) .0445(4)
C(1) .4343(11) .3046(5) 1.1449(10) .040(7)
C(2) .3012(12) .2942(5) 1.0055(11) .039(7)
C(3) .2941(13) .3441(4) .9045(11) .039(7)
N(4) .2819(8) .4051(4) .9637(8) .035(4)
C(5) .4122(11) .4137(5) 1.1039(10) .040(7)
C(6) .4208(12) .3649(5) 1.2070(11) .040(7)
O(7) .4266(8) .2600(3) 1.2443(8) .052(5)
C(8) .4969(11) .2078(4) 1.2496(11) .032(6)
O(9) .5704(9) .1986(3) 1.1845(8) .065(6)
C(10) .4587(11) .1620(4) 1.3386(11) .034(6)
O(11) .3130(7) .1391(3) 1.2495(7) .042(5)
C(41) .1313(11) .4120(6) .9741(13) .051(8)
C(42) .2917(13) .4512(5) .8637(12) .045(7)
C(12) .5787(9) .1131(4) 1.3811(9) .034(3)
C(13) .5451(16) .0566(4) 1.3196(14) .088(5)
C(14) .6549(15) .0118(7) 1.3592(17) .121(6)
C(15) .7968(16) .0222(5) 1.4670(15) .091(5)
C(16) .8371(12) .0796(4) 1.5213(12) .063(4)
C(17) .7261(9) .1240(5) 1.4788(11) .052(3)
C(18) .4455(10) .1860(4) 1.4663(10) .034(3)
C(19) .3587(11) .1532(5) 1.5206(10) .047(3)
C(20) .3503(14) .1711(5) 1.6454(11) .070(4)
C(21) .4254(13) .2225(5) 1.7143(13) .068(4)
C(22) .5110(13) .2549(5) 1.6580(13) .054(3)
C(23) .5208(12) .2364(5) 1.5370(11) .044(3)
H(1) .5370 .3022 1.1279 ?
H(21) .1976 .2935 1.0211 ?
H(22) .3154 .2521 .9625 ?
H(31) .3952 .3429 .8847 ?
H(32) .1964 .3373 .8078 ?
H(51) .5162 .4139 1.0889 ?
H(52) .3986 .4558 1.1470 ?
H(61) .5185 .3719 1.3036 ?
H(62) .3200 .3656 1.2273 ?
H(11) .3203 .1382 1.1598 ?
H(13) .4338 .0476 1.2404 ?
H(14) .6315 -.0313 1.3088 ?
H(15) .8765 -.0137 1.5094 ?
H(16) .9512 .0894 1.5940 ?
H(17) .7558 .1681 1.5227 ?
H(19) .2982 .1139 1.4678 ?
H(20) .2858 .1455 1.6894 ?
H(211) .4162 .2366 1.8093 ?
H(221) .5687 .2945 1.7118 ?
H(23) .5890 .2617 1.4965 ?
H(411) .1178 .3804 1.0460 ?
H(412) .0409 .4063 .8719 ?
H(413) .1281 .4566 1.0108 ?
H(421) .3978 .4477 .8531 ?
H(422) .2804 .4955 .8984 ?
H(423) .1998 .4427 .7639 ?
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
C(2) C(1) C(6) 110.0(9) yes
C(2) C(1) O(7) 107.9(8) yes
C(6) C(1) O(7) 105.4(8) yes
C(2) C(3) N(4) 111.7(8) yes
C(3) N(4) C(5) 109.6(8) yes
N(4) C(5) C(6) 112.5(8) yes
C(1) O(7) C(8) 117.0(8) yes
O(7) C(8) O(9) 122.6(9) yes
O(7) C(8) C(10) 111.7(8) yes
O(9) C(8) C(10) 125.0(10) yes
C(8) C(10) O(11) 105.3(8) yes
C(8) C(10) C(12) 108.6(8) yes
C(8) C(10) C(18) 115.5(8) yes
O(11) C(10) C(12) 112.2(8) yes
O(11) C(10) C(18) 107.0(8) yes
C(12) C(10) C(18) 109.2(8) yes
C(41) N(4) C(3) 110.8(8) yes
C(41) N(4) C(5) 111.6(8) yes
C(42) N(4) C(3) 107.4(8) yes
C(42) N(4) C(5) 109.0(8) yes
C(42) N(4) C(41) 108.3(8) yes
C(13) C(12) C(10) 120.7(9) yes
C(17) C(12) C(10) 121.1(8) yes
C(17) C(12) C(13) 118.2(10) yes
C(14) C(13) C(12) 120.6(14) yes
C(15) C(14) C(13) 119.8(16) yes
C(16) C(15) C(14) 120.2(15) yes
C(17) C(16) C(15) 118.4(12) yes
C(16) C(17) C(12) 122.1(10) yes
C(19) C(18) C(10) 117.1(9) yes
C(23) C(18) C(10) 123.8(8) yes
C23 C18 C19 119.1(10) yes
C20 C19 C18 119.9(10) yes
C21 C20 C19 120.2(11) yes
C22 C21 C20 119.0(12) yes
C23 C22 C21 120.4(12) yes
C22 C23 C18 121.4(11) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C(1) C(2) 1.520(10) yes
C(1) C(6) 1.530(10) yes
C(2) C(3) 1.520(10) yes
C(3) N(4) 1.530(10) yes
N(4) C(5) 1.510(10) yes
N(4) C(41) 1.510(10) yes
N(4) C(42) 1.500(10) yes
C(5) C(6) 1.520(10) yes
C(1) O(7) 1.470(10) yes
O(7) C(8) 1.350(10) yes
C(8) O(9) 1.180(10) yes
C(8) C(10) 1.530(10) yes
C(10) O(11) 1.440(10) yes
C(10) C(12) 1.530(10) yes
C(10) C(18) 1.490(10) yes
C(12) C(17) 1.4000(10) yes
C(12) C(13) 1.4000(10) yes
C(14) C(15) 1.4000(10) yes
C(15) C(16) 1.4000(10) yes
C(16) C(17) 1.4000(10) yes
C(10) C(18) 1.494(13) yes
C(18) C(19) 1.4000(10) yes
C(18) C(23) 1.386(13) yes
C(19) C(20) 1.4000(10) yes
C(20) C(21) 1.4000(10) yes
C(21) C(22) 1.4000(10) yes
C(22) C(23) 1.372(15) yes
