#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/70/2017065.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_2017065
loop_
_publ_author_name
'Kumarasinghe, Isuru R.'
'Hruby, Victor J.'
'Nichol, Gary S.'
_publ_section_title
;
 3-[5-(4-Chlorophenyl)-1-(4-methoxyphenyl)-1H-pyrazol-3-yl]propionic
 acid and the corresponding methyl ester
;
_journal_coeditor_code           SK3306
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o163
_journal_page_last               o166
_journal_paper_doi               10.1107/S010827010900941X
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C19 H17 Cl N2 O3'
_chemical_formula_moiety         'C19 H17 Cl N2 O3'
_chemical_formula_sum            'C19 H17 Cl N2 O3'
_chemical_formula_weight         356.80
_chemical_name_systematic
;3-[5-(4-Chlorophenyl)-1-(4-methoxyphenyl)-1H-pyrazol-3-yl]propionic
 acid
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                103.733(3)
_cell_angle_beta                 96.928(3)
_cell_angle_gamma                98.459(3)
_cell_formula_units_Z            4
_cell_length_a                   9.131(2)
_cell_length_b                   13.759(3)
_cell_length_c                   14.264(3)
_cell_measurement_reflns_used    5841
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.00
_cell_measurement_theta_min      2.40
_cell_volume                     1699.2(6)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics
;
DIAMOND (Brandenburg & Putz, 1999) and Mercury (Version 2.2; Macrae
et al.,  2008)
;
_computing_publication_material
;
SHELXTL (Sheldrick, 2008), publCIF (Westrip, 2008) and local
programs
;
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Bruker APEXII CCD diffractometer'
_diffrn_measurement_method       'thin-slice ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0246
_diffrn_reflns_av_sigmaI/netI    0.0351
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            19183
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         28.26
_diffrn_reflns_theta_min         2.29
_exptl_absorpt_coefficient_mu    0.246
_exptl_absorpt_correction_T_max  0.9735
_exptl_absorpt_correction_T_min  0.9155
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.522
_refine_diff_density_min         -0.322
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     461
_refine_ls_number_reflns         8218
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0601
_refine_ls_R_factor_gt           0.0426
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0500P)²+0.4502P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1053
_refine_ls_wR_factor_ref         0.1148
_reflns_number_gt                6174
_reflns_number_total             8218
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sk3306.cif
_cod_data_source_block           I
_cod_database_code               2017065
_cod_database_fobs_code          2017065
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl1 -0.27614(5) -0.31833(3) 0.67484(4) 0.04131(13) Uani d . 1 . .
O O1 0.04617(17) 0.19973(11) 1.08923(9) 0.0449(3) Uani d . 1 . .
O O2 0.62247(16) 0.45259(9) 0.56095(10) 0.0405(3) Uani d . 1 . .
H H2O 0.689(3) 0.479(2) 0.5275(19) 0.074(8) Uiso d . 1 . .
O O3 0.63158(14) 0.30375(9) 0.45893(9) 0.0337(3) Uani d . 1 . .
N N1 0.31218(15) 0.19334(10) 0.69068(10) 0.0255(3) Uani d . 1 . .
N N2 0.21733(15) 0.12475(10) 0.72088(10) 0.0244(3) Uani d . 1 . .
C C1 0.31393(18) 0.14856(12) 0.59717(11) 0.0244(3) Uani d . 1 . .
C C2 0.22024(18) 0.05316(12) 0.56672(12) 0.0262(3) Uani d . 1 . .
H H2 0.2024 0.0073 0.5035 0.031 Uiso calc R 1 . .
C C3 0.15901(17) 0.03923(11) 0.64726(11) 0.0234(3) Uani d . 1 . .
C C4 0.18565(17) 0.14963(12) 0.81879(11) 0.0234(3) Uani d . 1 . .
C C5 0.19647(19) 0.08145(13) 0.87649(13) 0.0300(4) Uani d . 1 . .
H H5 0.2357 0.0215 0.8538 0.036 Uiso calc R 1 . .
C C6 0.1502(2) 0.10115(14) 0.96662(13) 0.0339(4) Uani d . 1 . .
H H6 0.1559 0.0540 1.0054 0.041 Uiso calc R 1 . .
C C7 0.09518(19) 0.18974(14) 1.00096(12) 0.0304(4) Uani d . 1 . .
C C8 0.0912(2) 0.25997(13) 0.94570(12) 0.0304(4) Uani d . 1 . .
H H8 0.0583 0.3221 0.9702 0.036 Uiso calc R 1 . .
C C9 0.13575(19) 0.23892(12) 0.85421(12) 0.0285(4) Uani d . 1 . .
H H9 0.1317 0.2865 0.8158 0.034 Uiso calc R 1 . .
C C10 -0.0173(2) 0.28677(17) 1.12500(14) 0.0452(5) Uani d . 1 . .
H H10A 0.0596 0.3482 1.1384 0.068 Uiso calc R 1 . .
H H10B -0.0555 0.2820 1.1854 0.068 Uiso calc R 1 . .
H H10C -0.0999 0.2902 1.0759 0.068 Uiso calc R 1 . .
C C11 0.41458(19) 0.19607(12) 0.53809(12) 0.0278(4) Uani d . 1 . .
H H11A 0.3594 0.1847 0.4711 0.033 Uiso calc R 1 . .
H H11B 0.5022 0.1616 0.5329 0.033 Uiso calc R 1 . .
C C12 0.4701(2) 0.30929(12) 0.58101(13) 0.0311(4) Uani d . 1 . .
H H12A 0.3834 0.3448 0.5800 0.037 Uiso calc R 1 . .
H H12B 0.5167 0.3215 0.6501 0.037 Uiso calc R 1 . .
C C13 0.58203(19) 0.35346(12) 0.52660(13) 0.0284(4) Uani d . 1 . .
C C14 0.05165(17) -0.04738(12) 0.65634(12) 0.0236(3) Uani d . 1 . .
C C15 0.06232(19) -0.14580(12) 0.60665(12) 0.0293(4) Uani d . 1 . .
H H15 0.1400 -0.1557 0.5686 0.035 Uiso calc R 1 . .
C C16 -0.0378(2) -0.22898(13) 0.61177(12) 0.0306(4) Uani d . 1 . .
H H16 -0.0305 -0.2956 0.5769 0.037 Uiso calc R 1 . .
C C17 -0.14897(18) -0.21383(12) 0.66846(12) 0.0275(4) Uani d . 1 . .
C C18 -0.16246(18) -0.11766(13) 0.71918(13) 0.0294(4) Uani d . 1 . .
H H18 -0.2384 -0.1086 0.7588 0.035 Uiso calc R 1 . .
C C19 -0.06361(18) -0.03486(12) 0.71130(12) 0.0274(4) Uani d . 1 . .
H H19 -0.0744 0.0318 0.7439 0.033 Uiso calc R 1 . .
Cl Cl51 1.58948(6) 1.16094(4) 0.16067(5) 0.05287(16) Uani d . 1 . .
O O51 1.40228(16) 0.51734(10) -0.16297(9) 0.0411(3) Uani d . 1 . .
O O52 0.79956(16) 0.38456(9) 0.34517(10) 0.0391(3) Uani d . 1 . .
H H52O 0.747(3) 0.357(2) 0.379(2) 0.076(9) Uiso d . 1 . .
O O53 0.82523(16) 0.52788(9) 0.46318(10) 0.0414(3) Uani d . 1 . .
N N51 1.15524(15) 0.62669(10) 0.23265(10) 0.0275(3) Uani d . 1 . .
N N52 1.24349(15) 0.69184(10) 0.19441(10) 0.0257(3) Uani d . 1 . .
C C51 1.12167(18) 0.68508(12) 0.31247(12) 0.0269(3) Uani d . 1 . .
C C52 1.18747(19) 0.78708(12) 0.32632(12) 0.0279(4) Uani d . 1 . .
H H52 1.1807 0.8430 0.3785 0.034 Uiso calc R 1 . .
C C53 1.26365(18) 0.79014(12) 0.24948(12) 0.0248(3) Uani d . 1 . .
C C54 1.29342(18) 0.64860(12) 0.10536(11) 0.0239(3) Uani d . 1 . .
C C55 1.19538(19) 0.57000(12) 0.03676(12) 0.0289(4) Uani d . 1 . .
H H55 1.0997 0.5456 0.0507 0.035 Uiso calc R 1 . .
C C56 1.2366(2) 0.52766(13) -0.05103(13) 0.0317(4) Uani d . 1 . .
H H56 1.1695 0.4736 -0.0975 0.038 Uiso calc R 1 . .
C C57 1.3759(2) 0.56322(12) -0.07252(12) 0.0300(4) Uani d . 1 . .
C C58 1.4763(2) 0.63996(13) -0.00270(13) 0.0318(4) Uani d . 1 . .
H H58 1.5725 0.6638 -0.0163 0.038 Uiso calc R 1 . .
C C59 1.43537(19) 0.68140(13) 0.08681(12) 0.0285(4) Uani d . 1 . .
H H59 1.5046 0.7322 0.1353 0.034 Uiso calc R 1 . .
C C60 1.5382(2) 0.55308(15) -0.19046(15) 0.0435(5) Uani d . 1 . .
H H60A 1.5470 0.6260 -0.1859 0.065 Uiso calc R 1 . .
H H60B 1.5407 0.5163 -0.2579 0.065 Uiso calc R 1 . .
H H60C 1.6219 0.5420 -0.1468 0.065 Uiso calc R 1 . .
C C61 1.0217(2) 0.63930(12) 0.37321(12) 0.0292(4) Uani d . 1 . .
H H61A 0.9365 0.6759 0.3806 0.035 Uiso calc R 1 . .
H H61B 1.0790 0.6489 0.4393 0.035 Uiso calc R 1 . .
C C62 0.9610(2) 0.52670(13) 0.32904(13) 0.0325(4) Uani d . 1 . .
H H62A 0.9081 0.5169 0.2618 0.039 Uiso calc R 1 . .
H H62B 1.0463 0.4898 0.3246 0.039 Uiso calc R 1 . .
C C63 0.85545(19) 0.48111(12) 0.38645(12) 0.0283(4) Uani d . 1 . .
C C64 1.34394(18) 0.87970(12) 0.22497(12) 0.0247(3) Uani d . 1 . .
C C65 1.32780(19) 0.89161(13) 0.13001(12) 0.0280(4) Uani d . 1 . .
H H65 1.2646 0.8403 0.0786 0.034 Uiso calc R 1 . .
C C66 1.4031(2) 0.97761(13) 0.10989(14) 0.0324(4) Uani d . 1 . .
H H66 1.3925 0.9850 0.0450 0.039 Uiso calc R 1 . .
C C67 1.49379(19) 1.05237(13) 0.18537(14) 0.0320(4) Uani d . 1 . .
C C68 1.50994(19) 1.04394(13) 0.28041(14) 0.0319(4) Uani d . 1 . .
H H68 1.5717 1.0962 0.3318 0.038 Uiso calc R 1 . .
C C69 1.43416(18) 0.95756(12) 0.29928(13) 0.0275(3) Uani d . 1 . .
H H69 1.4440 0.9513 0.3645 0.033 Uiso calc R 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C7 O1 C10 . . 117.50(15) ?
H2O O2 C13 . . 111.6(16) ?
N2 N1 C1 . . 104.60(12) ?
N1 N2 C3 . . 111.96(13) ?
N1 N2 C4 . . 119.75(12) ?
C3 N2 C4 . . 128.23(13) ?
N1 C1 C2 . . 111.54(14) ?
N1 C1 C11 . . 121.68(14) ?
C2 C1 C11 . . 126.66(14) ?
C1 C2 H2 . . 127.1 ?
C1 C2 C3 . . 105.87(14) ?
H2 C2 C3 . . 127.1 ?
N2 C3 C2 . . 106.02(13) ?
N2 C3 C14 . . 124.92(14) ?
C2 C3 C14 . . 129.06(14) ?
N2 C4 C5 . . 120.45(14) ?
N2 C4 C9 . . 119.76(14) ?
C5 C4 C9 . . 119.68(15) ?
C4 C5 H5 . . 120.0 ?
C4 C5 C6 . . 119.95(16) ?
H5 C5 C6 . . 120.0 ?
C5 C6 H6 . . 119.9 ?
C5 C6 C7 . . 120.27(16) ?
H6 C6 C7 . . 119.9 ?
O1 C7 C6 . . 115.56(15) ?
O1 C7 C8 . . 124.64(16) ?
C6 C7 C8 . . 119.79(16) ?
C7 C8 H8 . . 120.2 ?
C7 C8 C9 . . 119.62(16) ?
H8 C8 C9 . . 120.2 ?
C4 C9 C8 . . 120.57(16) ?
C4 C9 H9 . . 119.7 ?
C8 C9 H9 . . 119.7 ?
O1 C10 H10A . . 109.5 ?
O1 C10 H10B . . 109.5 ?
O1 C10 H10C . . 109.5 ?
H10A C10 H10B . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
C1 C11 H11A . . 108.9 ?
C1 C11 H11B . . 108.9 ?
C1 C11 C12 . . 113.55(14) ?
H11A C11 H11B . . 107.7 ?
H11A C11 C12 . . 108.9 ?
H11B C11 C12 . . 108.9 ?
C11 C12 H12A . . 109.0 ?
C11 C12 H12B . . 109.0 ?
C11 C12 C13 . . 112.79(14) ?
H12A C12 H12B . . 107.8 ?
H12A C12 C13 . . 109.0 ?
H12B C12 C13 . . 109.0 ?
O2 C13 O3 . . 123.46(15) ?
O2 C13 C12 . . 112.14(15) ?
O3 C13 C12 . . 124.40(15) ?
C3 C14 C15 . . 119.34(14) ?
C3 C14 C19 . . 122.32(14) ?
C15 C14 C19 . . 118.33(14) ?
C14 C15 H15 . . 119.4 ?
C14 C15 C16 . . 121.17(15) ?
H15 C15 C16 . . 119.4 ?
C15 C16 H16 . . 120.5 ?
C15 C16 C17 . . 118.91(15) ?
H16 C16 C17 . . 120.5 ?
Cl1 C17 C16 . . 119.15(13) ?
Cl1 C17 C18 . . 119.27(13) ?
C16 C17 C18 . . 121.57(15) ?
C17 C18 H18 . . 120.6 ?
C17 C18 C19 . . 118.83(15) ?
H18 C18 C19 . . 120.6 ?
C14 C19 C18 . . 121.15(15) ?
C14 C19 H19 . . 119.4 ?
C18 C19 H19 . . 119.4 ?
C57 O51 C60 . . 117.74(15) ?
H52O O52 C63 . . 113.1(19) ?
N52 N51 C51 . . 105.06(13) ?
N51 N52 C53 . . 111.68(13) ?
N51 N52 C54 . . 116.90(13) ?
C53 N52 C54 . . 131.39(13) ?
N51 C51 C52 . . 111.09(14) ?
N51 C51 C61 . . 120.17(14) ?
C52 C51 C61 . . 128.72(15) ?
C51 C52 H52 . . 126.9 ?
C51 C52 C53 . . 106.29(14) ?
H52 C52 C53 . . 126.9 ?
N52 C53 C52 . . 105.87(14) ?
N52 C53 C64 . . 125.40(14) ?
C52 C53 C64 . . 128.63(15) ?
N52 C54 C55 . . 117.81(14) ?
N52 C54 C59 . . 122.19(14) ?
C55 C54 C59 . . 119.99(15) ?
C54 C55 H55 . . 120.0 ?
C54 C55 C56 . . 120.04(15) ?
H55 C55 C56 . . 120.0 ?
C55 C56 H56 . . 119.7 ?
C55 C56 C57 . . 120.53(16) ?
H56 C56 C57 . . 119.7 ?
O51 C57 C56 . . 115.14(15) ?
O51 C57 C58 . . 125.30(16) ?
C56 C57 C58 . . 119.56(15) ?
C57 C58 H58 . . 120.1 ?
C57 C58 C59 . . 119.76(16) ?
H58 C58 C59 . . 120.1 ?
C54 C59 C58 . . 119.99(15) ?
C54 C59 H59 . . 120.0 ?
C58 C59 H59 . . 120.0 ?
O51 C60 H60A . . 109.5 ?
O51 C60 H60B . . 109.5 ?
O51 C60 H60C . . 109.5 ?
H60A C60 H60B . . 109.5 ?
H60A C60 H60C . . 109.5 ?
H60B C60 H60C . . 109.5 ?
C51 C61 H61A . . 109.0 ?
C51 C61 H61B . . 109.0 ?
C51 C61 C62 . . 112.94(14) ?
H61A C61 H61B . . 107.8 ?
H61A C61 C62 . . 109.0 ?
H61B C61 C62 . . 109.0 ?
C61 C62 H62A . . 108.9 ?
C61 C62 H62B . . 108.9 ?
C61 C62 C63 . . 113.51(14) ?
H62A C62 H62B . . 107.7 ?
H62A C62 C63 . . 108.9 ?
H62B C62 C63 . . 108.9 ?
O52 C63 O53 . . 123.44(15) ?
O52 C63 C62 . . 112.68(14) ?
O53 C63 C62 . . 123.88(15) ?
C53 C64 C65 . . 122.27(15) ?
C53 C64 C69 . . 119.37(15) ?
C65 C64 C69 . . 118.30(15) ?
C64 C65 H65 . . 119.6 ?
C64 C65 C66 . . 120.72(16) ?
H65 C65 C66 . . 119.6 ?
C65 C66 H66 . . 120.4 ?
C65 C66 C67 . . 119.22(17) ?
H66 C66 C67 . . 120.4 ?
Cl51 C67 C66 . . 119.55(14) ?
Cl51 C67 C68 . . 118.90(14) ?
C66 C67 C68 . . 121.55(16) ?
C67 C68 H68 . . 120.7 ?
C67 C68 C69 . . 118.53(17) ?
H68 C68 C69 . . 120.7 ?
C64 C69 C68 . . 121.65(16) ?
C64 C69 H69 . . 119.2 ?
C68 C69 H69 . . 119.2 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C17 . 1.7379(16) ?
O1 C7 . 1.370(2) ?
O1 C10 . 1.420(2) ?
O2 H2O . 0.90(3) ?
O2 C13 . 1.314(2) ?
O3 C13 . 1.220(2) ?
N1 N2 . 1.3671(18) ?
N1 C1 . 1.333(2) ?
N2 C3 . 1.366(2) ?
N2 C4 . 1.432(2) ?
C1 C2 . 1.397(2) ?
C1 C11 . 1.501(2) ?
C2 H2 . 0.950 ?
C2 C3 . 1.377(2) ?
C3 C14 . 1.469(2) ?
C4 C5 . 1.393(2) ?
C4 C9 . 1.378(2) ?
C5 H5 . 0.950 ?
C5 C6 . 1.380(2) ?
C6 H6 . 0.950 ?
C6 C7 . 1.391(2) ?
C7 C8 . 1.386(2) ?
C8 H8 . 0.950 ?
C8 C9 . 1.391(2) ?
C9 H9 . 0.950 ?
C10 H10A . 0.980 ?
C10 H10B . 0.980 ?
C10 H10C . 0.980 ?
C11 H11A . 0.990 ?
C11 H11B . 0.990 ?
C11 C12 . 1.516(2) ?
C12 H12A . 0.990 ?
C12 H12B . 0.990 ?
C12 C13 . 1.500(2) ?
C14 C15 . 1.395(2) ?
C14 C19 . 1.393(2) ?
C15 H15 . 0.950 ?
C15 C16 . 1.378(2) ?
C16 H16 . 0.950 ?
C16 C17 . 1.381(2) ?
C17 C18 . 1.380(2) ?
C18 H18 . 0.950 ?
C18 C19 . 1.381(2) ?
C19 H19 . 0.950 ?
Cl51 C67 . 1.7490(17) ?
O51 C57 . 1.362(2) ?
O51 C60 . 1.402(2) ?
O52 H52O . 0.84(3) ?
O52 C63 . 1.315(2) ?
O53 C63 . 1.216(2) ?
N51 N52 . 1.3696(18) ?
N51 C51 . 1.326(2) ?
N52 C53 . 1.367(2) ?
N52 C54 . 1.427(2) ?
C51 C52 . 1.400(2) ?
C51 C61 . 1.504(2) ?
C52 H52 . 0.950 ?
C52 C53 . 1.373(2) ?
C53 C64 . 1.476(2) ?
C54 C55 . 1.389(2) ?
C54 C59 . 1.386(2) ?
C55 H55 . 0.950 ?
C55 C56 . 1.372(2) ?
C56 H56 . 0.950 ?
C56 C57 . 1.391(2) ?
C57 C58 . 1.394(2) ?
C58 H58 . 0.950 ?
C58 C59 . 1.388(2) ?
C59 H59 . 0.950 ?
C60 H60A . 0.980 ?
C60 H60B . 0.980 ?
C60 H60C . 0.980 ?
C61 H61A . 0.990 ?
C61 H61B . 0.990 ?
C61 C62 . 1.518(2) ?
C62 H62A . 0.990 ?
C62 H62B . 0.990 ?
C62 C63 . 1.500(2) ?
C64 C65 . 1.396(2) ?
C64 C69 . 1.393(2) ?
C65 H65 . 0.950 ?
C65 C66 . 1.387(2) ?
C66 H66 . 0.950 ?
C66 C67 . 1.382(3) ?
C67 C68 . 1.380(3) ?
C68 H68 . 0.950 ?
C68 C69 . 1.385(2) ?
C69 H69 . 0.950 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O2 H2O O53 . 0.90(3) 1.78(3) 2.6815(18) 178(3) y
O52 H52O O3 . 0.84(3) 1.84(3) 2.6790(18) 177(3) y
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C1 N1 N2 C3 . . . . -0.89(18) ?
C1 N1 N2 C4 . . . . -178.32(14) ?
N2 N1 C1 C2 . . . . 0.83(18) ?
N2 N1 C1 C11 . . . . -175.47(14) ?
N1 C1 C2 C3 . . . . -0.5(2) ?
C11 C1 C2 C3 . . . . 175.59(16) ?
N1 N2 C3 C2 . . . . 0.61(18) ?
N1 N2 C3 C14 . . . . -178.85(14) ?
C4 N2 C3 C2 . . . . 177.77(15) ?
C4 N2 C3 C14 . . . . -1.7(3) ?
C1 C2 C3 N2 . . . . -0.08(18) ?
C1 C2 C3 C14 . . . . 179.35(16) ?
N1 N2 C4 C5 . . . . -130.75(16) ?
N1 N2 C4 C9 . . . . 53.0(2) ?
C3 N2 C4 C5 . . . . 52.3(2) ?
C3 N2 C4 C9 . . . . -123.94(18) ?
N2 C4 C5 C6 . . . . -172.97(16) ?
C9 C4 C5 C6 . . . . 3.3(3) ?
C4 C5 C6 C7 . . . . -1.2(3) ?
C10 O1 C7 C6 . . . . -177.16(17) ?
C10 O1 C7 C8 . . . . 2.0(3) ?
C5 C6 C7 O1 . . . . 177.24(17) ?
C5 C6 C7 C8 . . . . -2.0(3) ?
O1 C7 C8 C9 . . . . -176.12(17) ?
C6 C7 C8 C9 . . . . 3.0(3) ?
N2 C4 C9 C8 . . . . 174.04(15) ?
C5 C4 C9 C8 . . . . -2.2(2) ?
C7 C8 C9 C4 . . . . -0.9(3) ?
N1 C1 C11 C12 . . . . -19.4(2) ?
C2 C1 C11 C12 . . . . 164.86(17) ?
C1 C11 C12 C13 . . . . 174.43(15) ?
C11 C12 C13 O2 . . . . 176.23(16) ?
C11 C12 C13 O3 . . . . -4.4(3) ?
N2 C3 C14 C15 . . . . -143.44(17) ?
N2 C3 C14 C19 . . . . 38.1(2) ?
C2 C3 C14 C15 . . . . 37.2(3) ?
C2 C3 C14 C19 . . . . -141.24(18) ?
C3 C14 C15 C16 . . . . -178.80(16) ?
C19 C14 C15 C16 . . . . -0.3(3) ?
C14 C15 C16 C17 . . . . -0.9(3) ?
C15 C16 C17 Cl1 . . . . 179.73(14) ?
C15 C16 C17 C18 . . . . 0.5(3) ?
Cl1 C17 C18 C19 . . . . -178.08(13) ?
C16 C17 C18 C19 . . . . 1.1(3) ?
C17 C18 C19 C14 . . . . -2.4(3) ?
C3 C14 C19 C18 . . . . -179.55(16) ?
C15 C14 C19 C18 . . . . 2.0(3) ?
C51 N51 N52 C53 . . . . -0.54(18) ?
C51 N51 N52 C54 . . . . -178.54(14) ?
N52 N51 C51 C52 . . . . -0.13(19) ?
N52 N51 C51 C61 . . . . 178.58(15) ?
N51 C51 C52 C53 . . . . 0.7(2) ?
C61 C51 C52 C53 . . . . -177.84(17) ?
N51 N52 C53 C52 . . . . 0.99(19) ?
N51 N52 C53 C64 . . . . -175.58(15) ?
C54 N52 C53 C52 . . . . 178.62(16) ?
C54 N52 C53 C64 . . . . 2.1(3) ?
C51 C52 C53 N52 . . . . -1.00(19) ?
C51 C52 C53 C64 . . . . 175.41(16) ?
N51 N52 C54 C55 . . . . 36.4(2) ?
N51 N52 C54 C59 . . . . -142.53(16) ?
C53 N52 C54 C55 . . . . -141.13(18) ?
C53 N52 C54 C59 . . . . 39.9(3) ?
N52 C54 C55 C56 . . . . 178.33(15) ?
C59 C54 C55 C56 . . . . -2.7(3) ?
C54 C55 C56 C57 . . . . -0.4(3) ?
C60 O51 C57 C56 . . . . 177.24(16) ?
C60 O51 C57 C58 . . . . -3.3(3) ?
C55 C56 C57 O51 . . . . -178.10(16) ?
C55 C56 C57 C58 . . . . 2.4(3) ?
O51 C57 C58 C59 . . . . 179.35(16) ?
C56 C57 C58 C59 . . . . -1.2(3) ?
N52 C54 C59 C58 . . . . -177.20(16) ?
C55 C54 C59 C58 . . . . 3.9(3) ?
C57 C58 C59 C54 . . . . -1.9(3) ?
N51 C51 C61 C62 . . . . -3.8(2) ?
C52 C51 C61 C62 . . . . 174.66(18) ?
C51 C61 C62 C63 . . . . -177.32(15) ?
C61 C62 C63 O52 . . . . 177.55(16) ?
C61 C62 C63 O53 . . . . -2.9(3) ?
N52 C53 C64 C65 . . . . 41.4(2) ?
N52 C53 C64 C69 . . . . -141.46(17) ?
C52 C53 C64 C65 . . . . -134.38(19) ?
C52 C53 C64 C69 . . . . 42.8(2) ?
C53 C64 C65 C66 . . . . 178.92(15) ?
C69 C64 C65 C66 . . . . 1.7(2) ?
C64 C65 C66 C67 . . . . -0.6(2) ?
C65 C66 C67 Cl51 . . . . 179.87(13) ?
C65 C66 C67 C68 . . . . -0.7(3) ?
Cl51 C67 C68 C69 . . . . -179.79(13) ?
C66 C67 C68 C69 . . . . 0.8(3) ?
C67 C68 C69 C64 . . . . 0.5(3) ?
C53 C64 C69 C68 . . . . -178.95(15) ?
C65 C64 C69 C68 . . . . -1.7(2) ?
