#------------------------------------------------------------------------------
#$Date: 2022-09-28 18:08:17 +0300 (Wed, 28 Sep 2022) $
#$Revision: 278247 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/10/13/2101341.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_2101341
loop_
_publ_author_name
'Sui, X.'
'Codding, P. W.'
_publ_section_title
;
 Structural and molecular modeling study of
 mono(pyrrolidiniomethyl)phenylacetate antiarrhythmic agents
;
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              803
_journal_page_last               810
_journal_paper_doi               10.1107/S0108768194014539
_journal_volume                  51
_journal_year                    1995
_chemical_formula_moiety         'C22 H25 N1 O4,C2 H2 O4'
_chemical_formula_sum            'C24 H27 N O8'
_chemical_formula_weight         457.5
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_type_scat_source
; Cromer & Mann (1968) for non-H atoms; Stewart,
Davidson & Simpson (1965) for H atoms
;
_cell_angle_alpha                95.447(4)
_cell_angle_beta                 106.614(4)
_cell_angle_gamma                82.653(4)
_cell_formula_units_Z            2
_cell_length_a                   8.3651(3)
_cell_length_b                   25.6280(10)
_cell_length_c                   5.5890(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293
_cell_measurement_theta_max      29.02
_cell_measurement_theta_min      21.37
_cell_volume                     1136.58(9)
_diffrn_measurement_device       'Enraf-Nonius CAD-4F'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.019
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            4758
_diffrn_reflns_theta_max         75
_diffrn_standards_decay_%        <10
_diffrn_standards_interval_time  3000s
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.8
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.387
_refine_diff_density_min         -0.32
_refine_ls_extinction_coef       1.37E-3(6)
_refine_ls_extinction_method     'Zachariasen (1967)'
_refine_ls_goodness_of_fit_obs   1.0886
_refine_ls_hydrogen_treatment    'see text'
_refine_ls_number_parameters     395
_refine_ls_number_reflns         3341
_refine_ls_R_factor_obs          0.055
_refine_ls_shift/esd_max         0.00786
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w=1/[σ²(F) + 0.00015F²]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_obs         0.059
_reflns_number_observed          3341
_reflns_number_total             4652
_reflns_observed_criterion       I>2.5\s(I)
_cod_data_source_file            cr0472.cif
_cod_data_source_block           cr0472c
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'w=1/[\s^2^(F) + 0.00015F^2^]'
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^(F) +
0.00015F^2^]'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        1136.60(10)
_cod_original_formula_sum        'C24 H27 N1 O8'
_cod_database_code               2101341
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
N(1) .3107(2) .39610(10) .1406(3) .0314(6)
C(2) .3060(3) .43680(10) .3494(4) .0412(8)
C(3) .2957(4) .48840(10) .2332(5) .0560(11)
C(4) .2187(3) .47730(10) -.0485(4) .0438(9)
C(5) .1849(3) .42010(10) -.0801(4) .0373(8)
C(6) .2809(3) .34240(10) .1906(5) .0451(9)
C(7) .3011(3) .30320(10) -.0179(5) .0453(8)
C(8) .4604(3) .28220(10) -.0283(5) .0474(9)
C(9) .4841(4) .24880(10) -.2291(5) .0575(11)
C(10) .3446(5) .23570(10) -.4176(5) .0726(14)
C(11) .1862(5) .25550(10) -.4063(6) .0766(14)
C(12) .1638(4) .28920(10) -.2096(6) .0629(12)
C(13) .6609(5) .22740(10) -.2372(8) .0779(17)
C(14) .7415(4) .19130(10) -.0319(7) .0699(14)
O(15) .8197(4) .20430(10) .1741(5) .1130(14)
O(16) .7083(3) .14150(10) -.1031(4) .0786(10)
C(17) .7809(7) .10410(10) .0863(9) .0911(19)
C(18) .7400(6) .05210(10) -.0104(8) .125(2)
C(19) .6823(8) .0329(2) -.2346(9) .175(3)
O(20) .6478(3) -.01880(10) -.2987(4) .0981(11)
C(21) .7214(4) -.05260(10) -.1123(6) .0668(13)
C(22) .8017(4) -.03430(10) .1234(6) .0664(13)
O(23) .8160(3) .01830(10) .1864(4) .0917(11)
C(24) .7118(5) -.10610(10) -.1657(8) .0878(17)
C(25) .7816(5) -.14080(10) .0166(7) .0872(18)
C(26) .8634(6) -.12300(10) .2509(7) .0878(18)
C(27) .8733(6) -.06970(10) .3057(7) .0891(18)
O(28) .6905(2) .37520(10) .4015(3) .0485(6)
O(29) .9303(2) .39970(10) .3799(3) .0703(9)
C(30) .7921(3) .38760(10) .2826(4) .0343(7)
C(31) .7134(3) .38690(10) -.0025(4) .0312(7)
O(32) .5622(2) .40060(10) -.0804(3) .0451(6)
O(33) .8142(2) .37360(10) -.1315(3) .0497(7)
H(1) .416(3) .3950(10) .112(4) 4.5(6)
H(21) .206(3) .4330(10) .401(4) 4.5(6)
H(22) .405(3) .4280(10) .494(4) 4.1(5)
H(31) .404(3) .5010(10) .257(5) 6.7(8)
H(32) .231(3) .5160(10) .306(5) 5.8(7)
H(41) .299(3) .4850(10) -.134(4) 4.5(6)
H(42) .116(3) .5010(10) -.111(4) 4.0(5)
H(51) .074(3) .4150(10) -.062(4) 3.8(5)
H(52) .199(3) .4000(10) -.229(4) 4.1(5)
H(61) .171(3) .3450(10) .214(4) 4.2(6)
H(62) .367(3) .3330(10) .351(4) 3.9(5)
H(8) .561(3) .2920(10) .106(4) 4.3(6)
H(10) .363(3) .2120(10) -.557(5) 6.5(7)
H(11) .093(4) .2470(10) -.544(6) 7.9(9)
H(12) .055(4) .3030(10) -.193(5) 6.0(8)
H(131) .648(4) .2090(10) -.409(7) 8.4(10)
H(132) .731(4) .2560(10) -.220(6) 8.3(11)
H(171) .896(6) .103(2) .131(9) 13.4(18)
H(172) .719(6) .117(2) .228(9) 13.5(18)
H(18) .602 .053 -.055 11.4
H(191) .574 .057 -.324 15.6
H(192) .778 .038 -.322 15.6
H(24) .647(4) -.1160(10) -.336(7) 8.9(10)
H(25) .770(4) -.1790(10) -.032(6) 9.0(10)
H(26) .928(5) -.148(2) .392(8) 11.2(13)
H(27) .940(4) -.0530(10) .463(6) 8.0(10)
H(28) .750(4) .3750(10) .592(6) 8.9(9)
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C(2) N(1) C(5) 103.2(2)
C(2) N(1) C(6) 114.2(2)
C(5) N(1) C(6) 114.9(2)
N(1) C(2) C(3) 104.0(2)
C(2) C(3) C(4) 105.4(2)
C(3) C(4) C(5) 105.7(2)
N(1) C(5) C(4) 103.4(2)
N(1) C(6) C(7) 110.8(2)
C(6) C(7) C(8) 119.8(2)
C(6) C(7) C(12) 121.3(2)
C(8) C(7) C(12) 118.8(2)
C(7) C(8) C(9) 121.2(2)
C(8) C(9) C(10) 118.6(3)
C(8) C(9) C(13) 119.8(3)
C(10) C(9) C(13) 121.6(3)
C(9) C(10) C(11) 120.6(3)
C(10) C(11) C(12) 120.5(3)
C(7) C(12) C(11) 120.3(3)
C(9) C(13) C(14) 110.8(4)
C(13) C(14) O(15) 125.6(3)
C(13) C(14) O(16) 111.5(3)
O(15) C(14) O(16) 122.9(3)
C(14) O(16) C(17) 114.9(3)
O(16) C(17) C(18) 110.3(3)
C(17) C(18) C(19) 131.6(4)
C(17) C(18) O(23) 106.4(3)
C(19) C(18) O(23) 120.3(3)
C(18) C(19) O(20) 124.8(4)
C(19) O(20) C(21) 114.1(3)
O(20) C(21) C(22) 121.3(3)
O(20) C(21) C(24) 118.8(3)
C(22) C(21) C(24) 119.9(3)
C(21) C(22) O(23) 122.3(3)
C(21) C(22) C(27) 119.5(3)
O(23) C(22) C(27) 118.2(3)
C(18) O(23) C(22) 115.1(2)
C(21) C(24) C(25) 120.3(3)
C(24) C(25) C(26) 120.2(4)
C(25) C(26) C(27) 119.8(3)
C(22) C(27) C(26) 120.4(3)
O(28) C(30) O(29) 124.9(2)
O(28) C(30) C(31) 112.7(2)
O(29) C(30) C(31) 122.3(2)
C(30) C(31) O(32) 118.0(2)
C(30) C(31) O(33) 115.2(2)
O(32) C(31) O(33) 126.8(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N(1) C(2) 1.495(3)
N(1) C(5) 1.498(2)
N(1) C(6) 1.496(3)
C(2) C(3) 1.510(4)
C(3) C(4) 1.535(3)
C(4) C(5) 1.512(3)
C(6) C(7) 1.498(3)
C(7) C(8) 1.387(4)
C(7) C(12) 1.387(4)
C(8) C(9) 1.390(4)
C(9) C(10) 1.384(4)
C(9) C(13) 1.522(5)
C(10) C(11) 1.373(5)
C(11) C(12) 1.375(5)
C(13) C(14) 1.493(5)
C(14) O(15) 1.190(4)
C(14) O(16) 1.340(4)
O(16) C(17) 1.444(5)
C(17) C(18) 1.435(5)
C(18) C(19) 1.282(6)
C(18) O(23) 1.416(5)
C(19) O(20) 1.385(5)
O(20) C(21) 1.372(4)
C(21) C(22) 1.365(4)
C(21) C(24) 1.383(5)
C(22) O(23) 1.373(4)
C(22) C(27) 1.380(5)
C(24) C(25) 1.366(5)
C(25) C(26) 1.358(5)
C(26) C(27) 1.379(5)
O(28) C(30) 1.303(3)
O(29) C(30) 1.196(3)
C(30) C(31) 1.540(3)
C(31) O(32) 1.230(2)
C(31) O(33) 1.255(3)
N(1) H(1) 0.93(3)
C(2) H(21) 0.98(3)
C(2) H(22) 0.99(2)
C(3) H(31) 0.97(3)
C(3) H(32) 0.96(3)
C(4) H(41) 0.98(3)
C(4) H(42) 0.97(2)
C(5) H(51) 0.99(2)
C(5) H(52) 0.96(2)
C(6) H(61) 0.95(3)
C(6) H(62) 1.01(2)
C(8) H(8) 1.00(2)
C(10) H(10) 0.98(3)
C(11) H(11) 0.96(3)
C(12) H(12) 0.96(3)
C(13) H(131) 1.01(4)
C(13) H(132) 0.97(4)
C(17) H(171) 0.92(5)
C(17) H(172) 1.07(6)
C(18) H(18) 1.10
C(19) H(191) 1.05
C(19) H(192) 1.08
C(24) H(24) 0.98(3)
C(25) H(25) 0.99(4)
C(26) H(26) 1.05(4)
C(27) H(27) 0.99(3)
O(28) H(28) 1.04(3)
