#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/24/2222426.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_2222426
loop_
_publ_author_name
'Zhang, Jin-Hua'
'Zuo, Hua'
'Xie, Yong-Sheng'
'Zhao, Bao-Xiang'
_publ_section_title
2-(4-Chlorophenyl)-5-(3,4-dimethoxyphenethyl)-6,7-dihydropyrazolo[1,5-a]pyrazin-4(5H)-one
_journal_coeditor_code           PV2160
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1457
_journal_paper_doi               10.1107/S1600536809020212
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C22 H22 Cl N3 O3'
_chemical_formula_moiety         'C22 H22 Cl N3 O3'
_chemical_formula_sum            'C22 H22 Cl N3 O3'
_chemical_formula_weight         411.88
_chemical_name_systematic
;
2-(4-Chlorophenyl)-5-(3,4-dimethoxyphenethyl)-6,7-dihydropyrazolo[1,5-
a]pyrazin-4(5H)-one
;
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                81.156(3)
_cell_angle_beta                 77.150(2)
_cell_angle_gamma                72.278(2)
_cell_formula_units_Z            2
_cell_length_a                   7.1709(4)
_cell_length_b                   10.6982(5)
_cell_length_c                   13.9169(6)
_cell_measurement_reflns_used    2906
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.07
_cell_measurement_theta_min      3.02
_cell_volume                     987.24(8)
_computing_cell_refinement       'SAINT (Bruker, 2005)'
_computing_data_collection       'SMART (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_computing_molecular_graphics    'XP in SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0212
_diffrn_reflns_av_sigmaI/netI    0.0316
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8654
_diffrn_reflns_theta_full        26.40
_diffrn_reflns_theta_max         26.40
_diffrn_reflns_theta_min         2.01
_exptl_absorpt_coefficient_mu    0.223
_exptl_absorpt_correction_T_max  0.9780
_exptl_absorpt_correction_T_min  0.9161
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker 2005)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.201
_refine_diff_density_min         -0.297
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     326
_refine_ls_number_reflns         3999
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0612
_refine_ls_R_factor_gt           0.0412
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0564P)²+0.1941P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1026
_refine_ls_wR_factor_ref         0.1146
_reflns_number_gt                2969
_reflns_number_total             3999
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            pv2160.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        987.25(8)
_cod_database_code               2222426
_cod_database_fobs_code          2222426
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 Cl 0.20421(8) 0.95549(6) 0.40014(4) 0.06084(19) Uani d . 1 . .
N N1 -0.4397(2) 0.70036(14) 0.26041(11) 0.0390(4) Uani d . 1 . .
N N2 -0.5553(2) 0.69103(14) 0.19947(10) 0.0367(4) Uani d . 1 . .
N N3 -0.7921(2) 0.70588(15) 0.06451(11) 0.0390(4) Uani d . 1 . .
O O1 -0.7274(2) 0.89705(14) -0.00841(10) 0.0575(4) Uani d . 1 . .
O O2 -1.3542(2) 0.72159(14) -0.37111(10) 0.0533(4) Uani d . 1 . .
O O3 -0.9862(2) 0.58773(15) -0.41075(10) 0.0544(4) Uani d . 1 . .
C C1 0.0314(3) 0.91488(18) 0.34943(14) 0.0406(4) Uani d . 1 . .
C C2 -0.0785(3) 0.8341(2) 0.40461(15) 0.0450(5) Uani d . 1 . .
H H2 -0.065(3) 0.8025(19) 0.4699(15) 0.048(6) Uiso d . 1 . .
C C3 -0.2109(3) 0.79940(19) 0.36251(14) 0.0419(4) Uani d . 1 . .
H H3 -0.289(3) 0.744(2) 0.3994(15) 0.057(6) Uiso d . 1 . .
C C4 -0.2335(3) 0.84383(17) 0.26496(12) 0.0343(4) Uani d . 1 . .
C C5 -0.1236(3) 0.92790(18) 0.21187(14) 0.0390(4) Uani d . 1 . .
H H5 -0.135(3) 0.9556(19) 0.1468(15) 0.046(5) Uiso d . 1 . .
C C6 0.0084(3) 0.96339(19) 0.25367(14) 0.0411(4) Uani d . 1 . .
H H6 0.082(3) 1.019(2) 0.2150(15) 0.049(6) Uiso d . 1 . .
C C7 -0.3707(3) 0.80384(17) 0.21908(12) 0.0345(4) Uani d . 1 . .
C C8 -0.4449(3) 0.86047(19) 0.13250(13) 0.0367(4) Uani d . 1 . .
H H8 -0.421(3) 0.933(2) 0.0897(15) 0.047(6) Uiso d . 1 . .
C C9 -0.5643(3) 0.78601(17) 0.12271(12) 0.0344(4) Uani d . 1 . .
C C10 -0.6987(3) 0.80106(19) 0.05288(13) 0.0386(4) Uani d . 1 . .
C C11 -0.7288(4) 0.5823(2) 0.12678(16) 0.0499(5) Uani d . 1 . .
H H11B -0.842(3) 0.543(2) 0.1422(16) 0.058(6) Uiso d . 1 . .
H H11A -0.600(4) 0.519(2) 0.0875(17) 0.066(7) Uiso d . 1 . .
C C12 -0.6833(4) 0.6042(2) 0.22192(15) 0.0462(5) Uani d . 1 . .
H H12B -0.611(3) 0.522(2) 0.2536(15) 0.053(6) Uiso d . 1 . .
H H12A -0.811(4) 0.647(2) 0.2650(17) 0.069(7) Uiso d . 1 . .
C C13 -0.9414(3) 0.7191(2) 0.00409(15) 0.0424(5) Uani d . 1 . .
H H13B -1.051(3) 0.684(2) 0.0467(15) 0.052(6) Uiso d . 1 . .
C C14 -0.8546(3) 0.6485(3) -0.08922(16) 0.0488(5) Uani d . 1 . .
H H14B -0.807(4) 0.551(3) -0.0693(18) 0.073(7) Uiso d . 1 . .
H H14A -0.736(4) 0.676(2) -0.1225(17) 0.066(7) Uiso d . 1 . .
C C15 -0.9982(3) 0.67175(18) -0.16026(13) 0.0383(4) Uani d . 1 . .
C C16 -1.1963(3) 0.7426(2) -0.13969(14) 0.0416(4) Uani d . 1 . .
H H16 -1.255(3) 0.777(2) -0.0773(16) 0.056(6) Uiso d . 1 . .
C C17 -1.3206(3) 0.7617(2) -0.20844(15) 0.0429(5) Uani d . 1 . .
H H17 -1.458(3) 0.814(2) -0.1909(14) 0.047(6) Uiso d . 1 . .
C C18 -1.2466(3) 0.70993(17) -0.29847(14) 0.0392(4) Uani d . 1 . .
C C19 -1.0451(3) 0.63712(18) -0.32041(13) 0.0387(4) Uani d . 1 . .
C C20 -0.9246(3) 0.61940(19) -0.25182(14) 0.0399(4) Uani d . 1 . .
H H20 -0.793(4) 0.570(2) -0.2684(15) 0.056(6) Uiso d . 1 . .
C C21 -1.5441(3) 0.8157(2) -0.36227(18) 0.0613(6) Uani d . 1 . .
H H21A -1.6042 0.8145 -0.4172 0.092 Uiso calc R 1 . .
H H21B -1.5293 0.9018 -0.3621 0.092 Uiso calc R 1 . .
H H21C -1.6275 0.7944 -0.3016 0.092 Uiso calc R 1 . .
C C22 -0.7782(3) 0.5470(2) -0.45031(16) 0.0593(6) Uani d . 1 . .
H H22A -0.7578 0.5147 -0.5136 0.089 Uiso calc R 1 . .
H H22B -0.7124 0.4782 -0.4060 0.089 Uiso calc R 1 . .
H H22C -0.7243 0.6205 -0.4579 0.089 Uiso calc R 1 . .
H H13A -0.998(3) 0.813(2) -0.0122(14) 0.048(6) Uiso d . 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
N2 N1 C7 . . 104.41(13) ?
N1 N2 C9 . . 112.51(14) ?
N1 N2 C12 . . 123.74(14) ?
C9 N2 C12 . . 122.94(15) ?
C10 N3 C13 . . 119.09(15) ?
C10 N3 C11 . . 121.19(15) ?
C13 N3 C11 . . 119.25(15) ?
C18 O2 C21 . . 117.38(16) ?
C19 O3 C22 . . 118.05(15) ?
C2 C1 C6 . . 120.98(17) ?
C2 C1 Cl . . 119.85(14) ?
C6 C1 Cl . . 119.16(15) ?
C1 C2 C3 . . 119.31(18) ?
C1 C2 H2 . . 121.1(13) ?
C3 C2 H2 . . 119.6(13) ?
C2 C3 C4 . . 121.06(19) ?
C2 C3 H3 . . 120.8(13) ?
C4 C3 H3 . . 118.2(13) ?
C5 C4 C3 . . 118.22(16) ?
C5 C4 C7 . . 120.68(15) ?
C3 C4 C7 . . 121.10(16) ?
C6 C5 C4 . . 120.96(17) ?
C6 C5 H5 . . 120.4(12) ?
C4 C5 H5 . . 118.6(12) ?
C1 C6 C5 . . 119.42(18) ?
C1 C6 H6 . . 121.9(12) ?
C5 C6 H6 . . 118.7(12) ?
N1 C7 C8 . . 111.40(15) ?
N1 C7 C4 . . 120.36(15) ?
C8 C7 C4 . . 128.23(16) ?
C9 C8 C7 . . 104.71(16) ?
C9 C8 H8 . . 126.3(12) ?
C7 C8 H8 . . 129.0(12) ?
N2 C9 C8 . . 106.96(15) ?
N2 C9 C10 . . 120.98(15) ?
C8 C9 C10 . . 131.84(16) ?
O1 C10 N3 . . 123.38(16) ?
O1 C10 C9 . . 121.11(16) ?
N3 C10 C9 . . 115.44(15) ?
N3 C11 C12 . . 112.58(17) ?
N3 C11 H11B . . 106.1(12) ?
C12 C11 H11B . . 108.8(12) ?
N3 C11 H11A . . 109.6(12) ?
C12 C11 H11A . . 108.6(12) ?
H11B C11 H11A . . 111.2(18) ?
N2 C12 C11 . . 108.36(16) ?
N2 C12 H12B . . 107.4(13) ?
C11 C12 H12B . . 110.9(12) ?
N2 C12 H12A . . 109.6(14) ?
C11 C12 H12A . . 108.3(13) ?
H12B C12 H12A . . 112.2(19) ?
N3 C13 C14 . . 112.60(17) ?
N3 C13 H13B . . 107.6(12) ?
C14 C13 H13B . . 111.3(12) ?
N3 C13 H13A . . 107.0(12) ?
C14 C13 H13A . . 110.7(12) ?
H13B C13 H13A . . 107.4(17) ?
C13 C14 C15 . . 114.67(18) ?
C13 C14 H14B . . 108.3(14) ?
C15 C14 H14B . . 109.1(14) ?
C13 C14 H14A . . 108.0(14) ?
C15 C14 H14A . . 110.3(13) ?
H14B C14 H14A . . 106(2) ?
C16 C15 C20 . . 118.18(17) ?
C16 C15 C14 . . 123.66(17) ?
C20 C15 C14 . . 118.15(17) ?
C15 C16 C17 . . 121.03(18) ?
C15 C16 H16 . . 121.5(13) ?
C17 C16 H16 . . 117.4(13) ?
C18 C17 C16 . . 120.32(19) ?
C18 C17 H17 . . 122.1(12) ?
C16 C17 H17 . . 117.5(12) ?
O2 C18 C17 . . 125.43(18) ?
O2 C18 C19 . . 115.24(16) ?
C17 C18 C19 . . 119.32(17) ?
O3 C19 C20 . . 125.34(18) ?
O3 C19 C18 . . 115.07(15) ?
C20 C19 C18 . . 119.59(17) ?
C19 C20 C15 . . 121.57(19) ?
C19 C20 H20 . . 117.2(13) ?
C15 C20 H20 . . 121.2(13) ?
O2 C21 H21A . . 109.5 ?
O2 C21 H21B . . 109.5 ?
H21A C21 H21B . . 109.5 ?
O2 C21 H21C . . 109.5 ?
H21A C21 H21C . . 109.5 ?
H21B C21 H21C . . 109.5 ?
O3 C22 H22A . . 109.5 ?
O3 C22 H22B . . 109.5 ?
H22A C22 H22B . . 109.5 ?
O3 C22 H22C . . 109.5 ?
H22A C22 H22C . . 109.5 ?
H22B C22 H22C . . 109.5 ?
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
Cl C1 . 1.7416(18) ?
N1 N2 . 1.3439(19) ?
N1 C7 . 1.346(2) ?
N2 C9 . 1.355(2) ?
N2 C12 . 1.452(2) ?
N3 C10 . 1.352(2) ?
N3 C13 . 1.465(2) ?
N3 C11 . 1.470(2) ?
O1 C10 . 1.227(2) ?
O2 C18 . 1.372(2) ?
O2 C21 . 1.418(3) ?
O3 C19 . 1.368(2) ?
O3 C22 . 1.425(3) ?
C1 C2 . 1.378(3) ?
C1 C6 . 1.380(3) ?
C2 C3 . 1.383(3) ?
C2 H2 . 0.94(2) ?
C3 C4 . 1.396(2) ?
C3 H3 . 0.95(2) ?
C4 C5 . 1.394(3) ?
C4 C7 . 1.476(2) ?
C5 C6 . 1.382(3) ?
C5 H5 . 0.92(2) ?
C6 H6 . 0.95(2) ?
C7 C8 . 1.402(2) ?
C8 C9 . 1.374(2) ?
C8 H8 . 0.94(2) ?
C9 C10 . 1.474(2) ?
C11 C12 . 1.499(3) ?
C11 H11B . 0.99(2) ?
C11 H11A . 1.06(2) ?
C12 H12B . 0.97(2) ?
C12 H12A . 1.00(3) ?
C13 C14 . 1.516(3) ?
C13 H13B . 1.01(2) ?
C13 H13A . 0.97(2) ?
C14 C15 . 1.523(2) ?
C14 H14B . 1.01(3) ?
C14 H14A . 0.98(2) ?
C15 C16 . 1.380(3) ?
C15 C20 . 1.399(3) ?
C16 C17 . 1.401(3) ?
C16 H16 . 0.95(2) ?
C17 C18 . 1.377(3) ?
C17 H17 . 0.97(2) ?
C18 C19 . 1.407(3) ?
C19 C20 . 1.380(2) ?
C20 H20 . 0.93(2) ?
C21 H21A . 0.9600 ?
C21 H21B . 0.9600 ?
C21 H21C . 0.9600 ?
C22 H22A . 0.9600 ?
C22 H22B . 0.9600 ?
C22 H22C . 0.9600 ?
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
C5 H5 O1 2_475 0.92(2) 2.48(2) 3.341(2) 156.3(17)
C8 H8 O1 2_475 0.94(2) 2.39(2) 3.296(2) 161.4(19)
C11 H11B Cg1 2_365 0.99(2) 2.67(2) 3.413(2) 132.2(16)
C12 H12A Cg2 1_455 1.00(3) 2.77(2) 3.640(2) 146.2(17)
C21 H21B Cg2 2_375 0.96 2.98 3.531(2) 117
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24703379
