#------------------------------------------------------------------------------
#$Date: 2022-09-28 17:08:17 +0200 (Wed 28 de Sep de 2022) $
#$Revision: 278247 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/12/2001265.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_2001265
loop_
_publ_author_name
'Rodier, N.'
'Céolin, R.'
'Agafonov, V.'
'Toscani, S.'
'Dugué, J.'
'Nicolaï, E.'
'Teulon, J.-M.'
_publ_section_title
;Acide
 4-{6-chloro-3-(4-chlorobenzyl)imidazo[4,5-b]pyridin-2-yl}-3,3-diméthylbutanoïque
;
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              2034
_journal_page_last               2037
_journal_paper_doi               10.1107/S0108270193005001
_journal_volume                  49
_journal_year                    1993
_chemical_formula_sum            'C19 H19 Cl2 N3 O2'
_chemical_formula_weight         392.29
_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           IntTabIV
_cell_angle_alpha                91.637(8)
_cell_angle_beta                 111.561(7)
_cell_angle_gamma                96.030(9)
_cell_formula_units_Z            4
_cell_length_a                   11.3570(10)
_cell_length_b                   11.7330(10)
_cell_length_c                   15.2050(10)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    294
_cell_measurement_theta_max      39.83
_cell_measurement_theta_min      23.38
_cell_volume                     1868.9(3)
_diffrn_measurement_device       'Enraf-Nonius CAD-4'
_diffrn_measurement_method       θ/2θ
_diffrn_radiation_type           CuK\=\a
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            5538
_diffrn_reflns_theta_max         60
_diffrn_standards_decay_%        41.1
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    3.33
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            incolore
_exptl_crystal_density_diffrn    1.394
_exptl_crystal_description       parallélépipèdique
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.35(5)
_refine_diff_density_min         -0.32(5)
_refine_ls_goodness_of_fit_obs   1.79
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_number_parameters     602
_refine_ls_number_reflns         4578
_refine_ls_R_factor_obs          0.048
_refine_ls_shift/esd_max         0.08
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 1/{1+[(F-21.2)/163.7]²}'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_obs         0.050
_reflns_number_observed          4578
_reflns_number_total             5538
_reflns_observed_criterion       I>=3\s(I)
_cod_data_source_file            pa1048.cif
_cod_data_source_block           pa1048_structure_1_of_1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value '1/{1+[(F-21.2)/163.7]^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+[(F-21.2)/163.7]^2^}'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        1869.1(6)
_cod_database_code               2001265
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
N(101) .0903(2) .2357(2) .5403(2)
C(102) .1737(3) .2892(3) .5034(2)
N(103) .1200(2) .3621(2) .4413(2)
C(104) -.0050(3) .3568(3) .4362(2)
C(105) -.1057(3) .4132(3) .3836(2)
C(106) -.2166(3) .3861(4) .3982(3)
C(107) -.2265(3) .3068(4) .4617(3)
N(108) -.1305(3) .2502(3) .5137(2)
C(109) -.0240(3) .2789(3) .4980(2)
C(110) .1158(3) .1547(3) .6150(2)
C(111) .1813(3) .2139(3) .7131(2)
C(112) .2960(3) .1868(3) .7736(2)
C(113) .3557(3) .2385(4) .8644(2)
C(114) .2984(3) .3202(3) .8939(2)
C(115) .1840(4) .3490(4) .8354(2)
C(116) .1242(4) .2960(3) .7448(2)
C(117) .3068(3) .2629(3) .5299(2)
C(118) .3336(3) .1880(3) .4544(2)
C(119) .2375(3) .0793(3) .4254(2)
C(120) .2352(3) .0057(3) .3410(2)
O(121) .1185(2) -.0335(2) .28530(10)
O(122) .3281(2) -.0146(2) .3255(2)
C(123) .4696(3) .1605(4) .5017(2)
C(124) .3227(3) .2573(3) .3686(2)
Cl(125) -.35030(10) .45130(10) .33660(10)
Cl(126) .37180(10) .38580(10) 1.00830(7)
N(201) -.0642(2) .2390(2) .0193(2)
C(202) -.1383(3) .2140(3) -.0753(2)
N(203) -.0836(2) .1502(2) -.1186(2)
C(204) .0319(3) .1328(3) -.0504(2)
C(205) .1303(3) .0752(3) -.0542(2)
C(206) .2318(3) .0758(3) .0288(2)
C(207) .2363(3) .1306(3) .1134(2)
N(208) .1425(2) .1881(3) .1182(2)
C(209) .0457(3) .1867(3) .0368(2)
C(210) -.0852(3) .3119(3) .0917(2)
C(211) -.1648(3) .2514(3) .1410(2)
C(212) -.2883(3) .2753(3) .1229(2)
C(213) -.3605(3) .2226(3) .1703(2)
C(214) -.3076(3) .1479(3) .2361(2)
C(215) -.1847(3) .1242(3) .2567(2)
C(216) -.1135(3) .1760(3) .2087(2)
C(217) -.2639(3) .2546(3) -.1239(2)
C(218) -.2653(3) .3609(3) -.1823(2)
C(219) -.2224(4) .3287(3) -.2638(2)
C(220a) -.1573(6) .4400(6) -.2989(4)
C(220b) -.2538(6) .4163(6) -.3377(4)
O(221a) -.2435(4) .4709(4) -.3741(3)
O(221b) -.1406(4) .4797(4) -.3182(3)
O(222a) -.0502(4) .4918(4) -.2613(3)
O(222b) -.3489(4) .4325(4) -.4002(3)
C(223) -.4004(4) .3927(4) -.2204(3)
C(224) -.1765(3) .4618(3) -.1192(2)
Cl(225) .36175(8) .00702(9) .03215(6)
Cl(226) -.39889(8) .08310(10) .29588(6)
H(105) -.098(3) .461(3) .344(2)
H(107) -.307(4) .285(4) .467(3)
H(110) .168(3) .097(3) .605(2)
H('110) .027(3) .118(3) .607(2)
H(112) .329(3) .139(3) .752(2)
H(113) .442(3) .224(3) .906(2)
H(115) .144(3) .399(3) .857(2)
H(116) .036(3) .307(3) .705(2)
H(117) .335(3) .221(3) .594(2)
H('117) .364(3) .330(3) .545(2)
H(119) .149(3) .095(3) .409(2)
H('119) .257(3) .027(3) .479(2)
H(121) .115(3) -.075(3) .237(2)
H(123) .495(3) .114(3) .460(2)
H('123) .533(3) .231(3) .531(2)
H("123) .476(3) .118(3) .557(2)
H(124) .230(3) .265(3) .330(2)
H('124) .351(3) .215(3) .325(2)
H("124) .383(3) .330(3) .393(2)
H(205) .126(3) .041(3) -.108(2)
H(207) .320(3) .132(3) .176(2)
H(210) -.132(3) .374(3) .056(2)
H('210) .007(3) .343(3) .139(2)
H(212) -.331(3) .322(3) .076(2)
H(213) -.452(3) .235(3) .155(2)
H(215) -.147(3) .076(3) .303(2)
H(216) -.025(3) .166(3) .227(2)
H(217) -.304(3) .269(3) -.079(2)
H('217) -.324(3) .186(3) -.167(2)
H(219a) -.298 .292 -.317
H('219a) -.164 .274 -.244
H(219b) -.270 .254 -.294
H('219b) -.136 .322 -.241
H(221a) -.188 .544 -.393
H(223) -.410(3) .452(3) -.261(3)
H('223) -.459(3) .328(3) -.271(3)
H("223) -.431(3) .411(3) -.175(3)
H(224) -.080(3) .448(3) -.091(2)
H('224) -.181(3) .535(3) -.156(2)
H("224) -.198(3) .478(3) -.066(2)
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(102) N(101) C(109) 106.5(3) yes
C(102) N(101) C(110) 128.5(3) yes
C(109) N(101) C(110) 124.9(3) yes
N(101) C(102) N(103) 112.0(3) yes
N(101) C(102) C(117) 122.7(3) yes
N(103) C(102) C(117) 125.3(3) yes
C(102) N(103) C(104) 106.0(3) yes
N(103) C(104) C(105) 132.3(3) yes
N(103) C(104) C(109) 109.3(3) yes
C(105) C(104) C(109) 118.4(3) yes
C(104) C(105) C(106) 115.7(4) yes
C(105) C(106) C(107) 121.7(3) yes
C(105) C(106) Cl(125) 120.2(3) yes
C(107) C(106) Cl(125) 118.1(3) yes
C(106) C(107) N(108) 124.1(4) yes
C(107) N(108) C(109) 112.6(3) yes
N(101) C(109) C(104) 106.2(3) yes
N(101) C(109) N(108) 126.3(3) yes
C(104) C(109) N(108) 127.5(3) yes
N(101) C(110) C(111) 112.6(3) yes
C(110) C(111) C(112) 121.6(3) yes
C(110) C(111) C(116) 120.2(3) yes
C(112) C(111) C(116) 118.2(3) yes
C(111) C(112) C(113) 122.2(4) yes
C(112) C(113) C(114) 118.7(3) yes
C(113) C(114) C(115) 120.6(3) yes
C(113) C(114) Cl(126) 119.4(2) yes
C(115) C(114) Cl(126) 120.0(3) yes
C(114) C(115) C(116) 120.4(4) yes
C(111) C(116) C(115) 119.9(3) yes
C(102) C(117) C(118) 115.9(2) yes
C(117) C(118) C(119) 108.8(3) yes
C(117) C(118) C(123) 106.1(2) yes
C(117) C(118) C(124) 109.4(3) yes
(119) C(118) C(123) 111.8(3) yes
C(119) C(118) C(124) 110.8(2) yes
C(123) C(118) C(124) 109.7(3) yes
C(118) C(119) C(120) 116.0(3) yes
C(119) C(120) O(121) 111.5(3) yes
C(119) C(120) O(122) 125.2(2) yes
O(121) C(120) O(122) 123.3(3) yes
C(202) N(201) C(209) 106.6(2) yes
C(202) N(201) C(210) 130.0(2) yes
C(209) N(201) C(210) 123.3(2) yes
N(201) C(202) N(203) 112.1(2) yes
N(201) C(202) C(217) 124.3(3) yes
N(203) C(202) C(217) 123.5(2) yes
C(202) N(203) C(204) 105.9(2) yes
N(203) C(204) C(205) 132.3(3) yes
N(203) C(204) C(209) 109.9(3) yes
C(205) C(204) C(209) 117.9(2) yes
C(204) C(205) C(206) 116.0(3) yes
C(205) C(206) C(207) 122.2(3) yes
C(205) C(206) Cl(225) 119.9(3) yes
C(207) C(206) Cl(225) 117.9(2) yes
C(206) C(207) N(208) 122.7(2) yes
C(207) N(208) C(209) 113.8(3) yes
N(201) C(209) C(204) 105.4(2) yes
N(201) C(209) N(208) 127.1(3) yes
C(204) C(209) N(208) 127.5(3) yes
N(201) C(210) C(211) 114.7(2) yes
C(210) C(211) C(212) 120.7(3) yes
C(210) C(211) C(216) 120.4(3) yes
C(212) C(211) C(216) 118.8(3) yes
C(211) C(212) C(213) 120.9(3) yes
C(212) C(213) C(214) 118.9(2) yes
C(213) C(214) C(215) 121.4(3) yes
C(213) C(214) Cl(226) 118.4(3) yes
C(215) C(214) Cl(226) 120.1(3) yes
C(214) C(215) C(216) 119.5(3) yes
C(211) C(216) C(215) 120.4(3) yes
C(202) C(217) C(218) 116.6(3) yes
C(217) C(218) C(219) 108.2(3) yes
C(217) C(218) C(223) 108.1(3) yes
C(217) C(218) C(224) 110.1(2) yes
C(219) C(218) C(223) 111.0(3) yes
C(219) C(218) C(224) 110.6(3) yes
C(223) C(218) C(224) 108.8(3) yes
C(218) C(219) C(220a) 112.5(3) yes
C(218) C(219) C(220b) 110.7(4) yes
C(219) C(220a) O(221a) 107.5(5) yes
C(219) C(220b) O(221b) 102.7(4) yes
C(219) C(220a) O(222a) 128.7(5) yes
C(219) C(220b) O(222b) 133.5(6) yes
O(221a) C(220a) O(222a) 123.7(6) yes
O(221b) C(220b) O(222b) 123.8(6) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
N(101) C(102) 1.376(4) yes
N(101) C(109) 1.378(4) yes
N(101) C(110) 1.467(4) yes
C(102) N(103) 1.314(4) yes
C(102) C(117) 1.484(4) yes
N(103) C(104) 1.387(4) yes
C(104) C(105) 1.379(5) yes
C(104) C(109) 1.388(5) yes
C(105) C(106) 1.363(6) yes
C(106) C(107) 1.386(6) yes
C(106) Cl(125) 1.734(4) yes
C(107) N(108) 1.342(5) yes
N(108) C(109) 1.328(5) yes
C(110) C(111) 1.510(4) yes
C(111) C(112) 1.366(4) yes
C(111) C(116) 1.384(6) yes
C(112) C(113) 1.383(5) yes
C(113) C(114) 1.365(6) yes
C(114) C(115) 1.362(5) yes
C(114) Cl(126) 1.742(3) yes
C(115) C(116) 1.386(5) yes
C(117) C(118) 1.562(5) yes
C(118) C(119) 1.528(4) yes
C(118) C(123) 1.519(4) yes
C(118) C(124) 1.531(5) yes
C(119) C(120) 1.518(5) yes
C(120) O(121) 1.308(3) yes
C(120) O(122) 1.207(5) yes
N(201) C(202) 1.377(3) yes
N(201) C(209) 1.391(4) yes
N(201) C(210) 1.477(4) yes
C(202) N(203) 1.322(4) yes
C(202) C(217) 1.483(4) yes
N(203) C(204) 1.380(3) yes
C(204) C(205) 1.382(5) yes
C(204) C(209) 1.400(4) yes
C(205) C(206) 1.360(3) yes
C(206) C(207) 1.403(5) yes
C(206) Cl(225) 1.741(3) yes
C(207) N(208) 1.342(5) yes
N(208) C(209) 1.317(3) yes
C(210) C(211) 1.508(5) yes
C(211) C(212) 1.387(5) yes
C(211) C(216) 1.380(4) yes
C(212) C(213) 1.389(5) yes
C(213) C(214) 1.360(5) yes
C(214) C(215) 1.374(5) yes
C(214) Cl(226) 1.746(4) yes
C(215) C(216) 1.382(5) yes
C(217) C(218) 1.550(5) yes
C(218) C(219) 1.540(6) yes
C(218) C(223) 1.519(5) yes
C(218) C(224) 1.520(4) yes
C(219) C(220a) 1.632(8) yes
C(219) C(220b) 1.515(7) yes
C(220a) O(221a) 1.294(7) yes
C(220b) O(221b) 1.342(7) yes
C(220a) O(222a) 1.221(7) yes
C(220b) O(222b) 1.185(7) yes
C(105) H(105) 0.86(4) yes
C(107) H(107) 0.95(4) yes
C(110) H(110) 0.99(4) yes
C(110) H('110) 1.01(3) yes
C(112) H(112) 0.83(4) yes
C(113) H(113) 0.99(3) yes
C(115) H(115) 0.90(4) yes
C(116) H(116) 0.99(3) yes
C(117) H(117) 1.06(3) yes
C(117) H('117) 0.93(3) yes
C(119) H(119) 0.98(3) yes
C(119) H('119) 1.01(3) yes
O(121) H(121) 0.86(3) yes
C(123) H(123) 0.96(4) yes
C(123) H('123) 1.01(3) yes
C(123) H("123) 0.97(4) yes
C(124) H(124) 1.01(3) yes
C(124) H('124) 0.98(4) yes
C(124) H("124) 1.01(3) yes
C(205) H(205) 0.89(3) yes
C(207) H(207) 1.07(3) yes
C(210) H(210) 1.00(3) yes
C(210) H('210) 1.05(2) yes
C(212) H(212) 0.93(3) yes
C(213) H(213) 1.01(3) yes
C(215) H(215) 0.92(3) yes
C(216) H(216) 0.96(3) yes
C(217) H(217) 0.96(3) yes
C(217) H('217) 1.03(3) yes
C(219) H(219a) 0.98 yes
C(219) H(219b) 0.98 yes
C(219) H('219a) 0.95 yes
C(219) H('219b) 0.93 yes
O(221a) H(221a) 1.11 yes
C(223) H(223) 0.93(4) yes
C(223) H('223) 1.05(3) yes
C(223) H("223) 0.91(5) yes
C(224) H(224) 1.06(3) yes
C(224) H('224) 1.04(3) yes
C(224) H("224) 0.95(4) yes
