#------------------------------------------------------------------------------
#$Date: 2018-09-27 07:13:35 +0300 (Thu, 27 Sep 2018) $
#$Revision: 211196 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/05/7220533.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7220533
loop_
_publ_author_name
'Neto, Brenno A. D.'
'Silva, Gabriel C.O.'
'Corrêa, José'
'Rodrigues, marcelo Oliveira'
'Alvim, Haline G. O.'
'Guido, Bruna C.'
'Gatto, Claudia C.'
'Wanderley, Kaline'
'Fioramonte, Mariana'
'Gozzo, Fabio Cesar'
'de Souza, Rodrigo Octavio M. A.'
_publ_section_title
;
 The Biginelli Reaction under Batch and Continuous Flow Conditions:
 Catalysis, Mechanism and Antitumoral Activity
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C5RA07677C
_journal_year                    2015
_chemical_formula_moiety         'C8 H2 Cl2 O4 Zn'
_chemical_formula_sum            'C8 H2 Cl2 O4 Zn'
_chemical_formula_weight         298.37
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_creation_date             2014-03-27T10:45:52-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2014-08-20 deposited with the CCDC.
2015-05-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.0140(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.9914(4)
_cell_length_b                   7.1576(2)
_cell_length_c                   7.4801(2)
_cell_measurement_reflns_used    6701
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      31.11
_cell_measurement_theta_min      2.43
_cell_measurement_wavelength     0.71073
_cell_volume                     898.48(4)
_computing_cell_refinement       'SAINT V8.18C (Bruker AXS Inc.)'
_computing_data_collection       'Bruker Instrument Service v2011.2.0.0'
_computing_data_reduction        'SAINT V8.18C (Bruker AXS Inc.)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.99
_diffrn_measured_fraction_theta_max 0.99
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0271
_diffrn_reflns_av_unetI/netI     0.0244
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            12695
_diffrn_reflns_theta_full        31.19
_diffrn_reflns_theta_max         31.19
_diffrn_reflns_theta_min         2.43
_exptl_absorpt_coefficient_mu    3.312
_exptl_absorpt_correction_T_max  0.7245
_exptl_absorpt_correction_T_min  0.2688
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.206
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.56
_refine_diff_density_min         -0.495
_refine_diff_density_rms         0.076
_refine_ls_extinction_coef       0.0174(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.04
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2885
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.04
_refine_ls_R_factor_all          0.0306
_refine_ls_R_factor_gt           0.0247
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0268P)²+0.5254P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0578
_refine_ls_wR_factor_ref         0.0604
_reflns_number_gt                2545
_reflns_number_total             2885
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ra07677c2.cif
_cod_data_source_block           shelx
_cod_original_sg_symbol_H-M      P121/c1
_cod_database_code               7220533
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
Zn1 Zn 0.434222(10) 0.73134(2) 0.35020(2) 0.01604(7) Uani 1 1 d
Cl2 Cl 0.06107(3) 0.20664(9) 0.37552(10) 0.04945(16) Uani 1 1 d
Cl1 Cl 0.11340(3) 0.63114(8) 0.43285(11) 0.05573(19) Uani 1 1 d
C4 C 0.29541(8) 0.1700(2) 0.52641(19) 0.0145(3) Uani 1 1 d
C5 C 0.31939(8) 0.3563(2) 0.54608(19) 0.0141(3) Uani 1 1 d
C6 C 0.26210(9) 0.4965(2) 0.5182(2) 0.0199(3) Uani 1 1 d
C1 C 0.18240(9) 0.4531(2) 0.4675(2) 0.0245(3) Uani 1 1 d
C2 C 0.15894(9) 0.2673(2) 0.4448(3) 0.0241(3) Uani 1 1 d
C3 C 0.21547(9) 0.1267(2) 0.4756(2) 0.0218(3) Uani 1 1 d
C7 C 0.40572(8) 0.4062(2) 0.59470(19) 0.0133(3) Uani 1 1 d
O1 O 0.42791(6) 0.57470(15) 0.58571(14) 0.0172(2) Uani 1 1 d
O2 O 0.54788(7) 0.72719(15) 0.35648(17) 0.0201(2) Uani 1 1 d
O4 O 0.35747(7) 0.57078(17) 0.20704(15) 0.0216(2) Uani 1 1 d
O3 O 0.38477(8) 0.95703(17) 0.42544(15) 0.0251(3) Uani 1 1 d
H3 H 0.1960(14) 0.002(4) 0.454(3) 0.039(6) Uiso 1 1 d
C8 C 0.35225(8) 1.0075(2) 0.55669(19) 0.0140(3) Uani 1 1 d
H6 H 0.2789(11) 0.625(3) 0.534(3) 0.024(5) Uiso 1 1 d
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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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'
Zn Zn 0.2839 1.4301 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
O2 Zn1 O4 126.31(5) . .
O2 Zn1 O3 118.90(5) . .
O4 Zn1 O3 111.71(6) . .
O2 Zn1 O1 98.85(5) . .
O4 Zn1 O1 91.64(5) . .
O3 Zn1 O1 96.85(5) . .
O2 Zn1 O1 86.80(4) . 4_575
O4 Zn1 O1 87.03(4) . 4_575
O3 Zn1 O1 78.05(4) . 4_575
O1 Zn1 O1 173.79(5) . 4_575
C3 C4 C5 119.96(14) . .
C3 C4 C8 116.52(14) . 1_545
C5 C4 C8 123.52(13) . 1_545
C6 C5 C4 119.19(14) . .
C6 C5 C7 120.00(13) . .
C4 C5 C7 120.81(13) . .
C1 C6 C5 120.76(15) . .
C1 C6 H6 120.4(12) . .
C5 C6 H6 118.9(12) . .
C6 C1 C2 119.83(15) . .
C6 C1 Cl1 119.28(14) . .
C2 C1 Cl1 120.89(13) . .
C3 C2 C1 119.74(15) . .
C3 C2 Cl2 118.68(13) . .
C1 C2 Cl2 121.57(13) . .
C2 C3 C4 120.49(15) . .
C2 C3 H3 116.0(14) . .
C4 C3 H3 123.4(14) . .
O2 C7 O1 124.06(13) 3_666 .
O2 C7 C5 115.82(13) 3_666 .
O1 C7 C5 120.11(13) . .
C7 O1 Zn1 127.25(9) . .
C7 O1 Zn1 118.71(9) . 4_576
Zn1 O1 Zn1 112.29(5) . 4_576
C7 O2 Zn1 126.93(10) 3_666 .
C8 O4 Zn1 135.52(10) 4_575 .
C8 O3 Zn1 136.88(11) . .
O4 C8 O3 126.84(14) 4_576 .
O4 C8 C4 115.83(12) 4_576 1_565
O3 C8 C4 117.12(13) . 1_565
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Zn1 O2 1.9246(11) .
Zn1 O4 1.9315(11) .
Zn1 O3 1.9443(11) .
Zn1 O1 2.1050(10) .
Zn1 O1 2.4055(11) 4_575
Cl2 C2 1.7183(17) .
Cl1 C1 1.7235(17) .
C4 C3 1.387(2) .
C4 C5 1.395(2) .
C4 C8 1.506(2) 1_545
C5 C6 1.391(2) .
C5 C7 1.498(2) .
C6 C1 1.383(2) .
C6 H6 0.97(2) .
C1 C2 1.391(3) .
C2 C3 1.385(2) .
C3 H3 0.96(2) .
C7 O2 1.2555(18) 3_666
C7 O1 1.2686(18) .
O1 Zn1 2.4055(11) 4_576
O2 C7 1.2554(18) 3_666
O4 C8 1.2471(18) 4_575
O3 C8 1.2528(17) .
C8 O4 1.2471(18) 4_576
C8 C4 1.506(2) 1_565
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
C3 C4 C5 C6 1.4(2) . .
C8 C4 C5 C6 -178.86(14) 1_545 .
C3 C4 C5 C7 -177.91(14) . .
C8 C4 C5 C7 1.8(2) 1_545 .
C4 C5 C6 C1 -1.5(2) . .
C7 C5 C6 C1 177.90(15) . .
C5 C6 C1 C2 0.3(3) . .
C5 C6 C1 Cl1 -179.57(13) . .
C6 C1 C2 C3 0.9(3) . .
Cl1 C1 C2 C3 -179.24(14) . .
C6 C1 C2 Cl2 -178.03(14) . .
Cl1 C1 C2 Cl2 1.8(2) . .
C1 C2 C3 C4 -0.9(3) . .
Cl2 C2 C3 C4 178.06(13) . .
C5 C4 C3 C2 -0.3(2) . .
C8 C4 C3 C2 -179.98(15) 1_545 .
C6 C5 C7 O2 169.85(14) . 3_666
C4 C5 C7 O2 -10.8(2) . 3_666
C6 C5 C7 O1 -9.9(2) . .
C4 C5 C7 O1 169.42(13) . .
O2 C7 O1 Zn1 107.42(15) 3_666 .
C5 C7 O1 Zn1 -72.81(16) . .
O2 C7 O1 Zn1 -88.86(15) 3_666 4_576
C5 C7 O1 Zn1 90.91(14) . 4_576
O2 Zn1 O1 C7 -104.46(12) . .
O4 Zn1 O1 C7 22.70(12) . .
O3 Zn1 O1 C7 134.79(12) . .
O1 Zn1 O1 C7 100.2(3) 4_575 .
O2 Zn1 O1 Zn1 90.95(5) . 4_576
O4 Zn1 O1 Zn1 -141.89(5) . 4_576
O3 Zn1 O1 Zn1 -29.80(6) . 4_576
O1 Zn1 O1 Zn1 -64.4(4) 4_575 4_576
O4 Zn1 O2 C7 -61.41(15) . 3_666
O3 Zn1 O2 C7 140.17(13) . 3_666
O1 Zn1 O2 C7 37.23(14) . 3_666
O1 Zn1 O2 C7 -145.36(14) 4_575 3_666
O2 Zn1 O4 C8 -32.10(18) . 4_575
O3 Zn1 O4 C8 127.63(15) . 4_575
O1 Zn1 O4 C8 -134.33(15) . 4_575
O1 Zn1 O4 C8 51.74(15) 4_575 4_575
O2 Zn1 O3 C8 -109.18(17) . .
O4 Zn1 O3 C8 89.42(17) . .
O1 Zn1 O3 C8 -5.10(17) . .
O1 Zn1 O3 C8 171.30(17) 4_575 .
Zn1 O3 C8 O4 17.2(3) . 4_576
Zn1 O3 C8 C4 -157.32(12) . 1_565
