#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/33/09/4330997.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_4330997
loop_
_publ_author_name
'Monami Maiti'
'Dipali Sadhukhan'
'Santarupa Thakurta'
'Syamantak Roy'
'Guillaume Pilet'
'Ray J. Butcher'
'Aline Nonat'
'Loïc J. Charbonnière'
'Samiran Mitra'
_publ_section_title
;
 Series of Dicyanamide-Interlaced Assembly of Zinc-Schiff-Base Complexes:
 Crystal Structure and Photophysical and Thermal Studies
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              12176
_journal_page_last               12187
_journal_paper_doi               10.1021/ic3012958
_journal_volume                  51
_journal_year                    2012
_chemical_formula_moiety         'C19 H14 Cl2 N5 O2 Zn1.50'
_chemical_formula_sum            'C19 H14 Cl2 N5 O2 Zn1.5'
_chemical_formula_weight         513.33
_space_group_IT_number           60
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_space_group_name_H-M   'P b c n'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   22.058(5)
_cell_length_b                   8.565(5)
_cell_length_c                   21.175(5)
_cell_measurement_reflns_used    7974
_cell_measurement_temperature    293
_cell_measurement_theta_max      29
_cell_measurement_theta_min      2
_cell_volume                     4001(3)
_computing_cell_refinement       'CrysAlis, (Oxford Diffraction, 2002)'
_computing_data_collection       'Gemini, (Oxford Diffraction, 2006)'
_computing_data_reduction        'CrysAlis, (Oxford Diffraction, 2002)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      293
_diffrn_measured_fraction_theta_full 0.957
_diffrn_measured_fraction_theta_max 0.861
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Oxford Diffraction Gemini'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.071
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            17965
_diffrn_reflns_theta_full        25.206
_diffrn_reflns_theta_max         29.310
_diffrn_reflns_theta_min         1.846
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.107
_exptl_absorpt_correction_T_max  0.80
_exptl_absorpt_correction_T_min  0.67
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
; 
 Analytical Absorption (De Meulenaer & Tompa, 1965) 
;
_exptl_crystal_colour            color
_exptl_crystal_density_diffrn    1.704
_exptl_crystal_description       cubic
_exptl_crystal_F_000             2064
_exptl_crystal_size_max          0.231
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.105
_refine_diff_density_max         1.12
_refine_diff_density_min         -1.01
_refine_ls_extinction_coef       11(12)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_refine_ls_goodness_of_fit_ref   1.0949
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     286
_refine_ls_number_reflns         3647
_refine_ls_number_restraints     33
_refine_ls_R_factor_all          0.0543
_refine_ls_R_factor_gt           0.0447
_refine_ls_shift/su_max          0.0012234
_refine_ls_shift/su_mean         0.0000332
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 6.18 1.10 4.03 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0513
_refine_ls_wR_factor_gt          0.0486
_refine_ls_wR_factor_ref         0.0482
_reflns_limit_h_max              27
_reflns_limit_h_min              0
_reflns_limit_k_max              11
_reflns_limit_k_min              0
_reflns_limit_l_max              28
_reflns_limit_l_min              0
_reflns_number_gt                3940
_reflns_number_total             4720
_reflns_threshold_expression     I>2.0σ(I)
_oxford_diffrn_Wilson_B_factor   2.44
_oxford_diffrn_Wilson_scale      0.36
_oxford_refine_ls_r_factor_ref   0.0414
_oxford_refine_ls_scale          1.790(4)
_oxford_reflns_number_all        4704
_oxford_reflns_threshold_expression_ref I>3.0\s(I)
_cod_data_source_file            ic3012958_si_002_1.cif
_cod_data_source_block           1
_cod_original_sg_symbol_H-M      'P b c n '
_cod_original_formula_sum        'C19 H14 Cl2 N5 O2 Zn1.50'
_cod_database_code               4330997
#BEGIN Tags that were not found in dictionaries:
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S, U'S 
CONT EXTPARAM 
RIDE C   (   3,X'S) H   (  31,X'S) 
RIDE C   (   4,X'S) H   (  41,X'S) 
RIDE C   (   7,X'S) H   (  71,X'S) 
RIDE C   (   9,X'S) H   (  91,X'S) 
RIDE C   (  11,X'S) H   ( 112,X'S) H   ( 111,X'S) 
RIDE C   (  12,X'S) H   ( 121,X'S) H   ( 122,X'S) 
RIDE C   (  13,X'S) H   ( 132,X'S) H   ( 131,X'S) 
RIDE C   (  15,X'S) H   ( 151,X'S) 
RIDE C   (  17,X'S) H   ( 171,X'S) 
RIDE C   (  20,X'S) H   ( 201,X'S) 
RIDE C   (  21,X'S) H   ( 211,X'S) 
END                                                                             
;
_iucr_refine_instruction_details_restraints
;
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
DISTANCE 1.300000 , 0.002000 = N(43) TO C(46) 
DISTANCE 1.300000 , 0.002000 = N(43) TO C(44) 
DISTANCE 1.200000 , 0.020000 = C(46) TO N(47) 
U(IJ)'S  0.0, 0.010000 = C(44) TO N(45) 
U(IJ)'S  0.0, 0.010000 = C(44) TO N(43) 
U(IJ)'S  0.0, 0.010000 = C(42) TO N(43) 
U(IJ)'S  0.0, 0.010000 = C(46) TO N(43) 
U(IJ)'S  0.0, 0.010000 = C(46) TO N(47) 
END                                                                             
;
#END Tags that were not found in dictionaries
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
x,-y,z+1/2
-x,y,-z+1/2
-x+1/2,-y+1/2,z+1/2
x+1/2,y+1/2,-z+1/2
x+1/2,-y+1/2,-z
-x+1/2,y+1/2,z
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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
N41 N 0.62215(15) 0.1557(4) 0.82504(17) 0.0506 1.0000 Uani . .
C42 C 0.6079(2) 0.0324(6) 0.8256(3) 0.0680 1.0000 Uani . U
N43 N 0.6044(3) -0.1191(6) 0.8253(3) 0.1130 1.0000 Uani D U
N45 N 0.5158(3) -0.2808(7) 0.7813(4) 0.0568 0.5000 Uani . U
C44 C 0.5544(4) -0.1920(11) 0.8106(6) 0.0832 0.5000 Uani D U
C46 C 0.5613(5) -0.1958(18) 0.8531(6) 0.1019 0.5000 Uani D U
N47 N 0.5284(5) -0.2771(12) 0.8697(6) 0.1056 0.5000 Uani D U
O1 O 0.51649(9) 0.3768(3) 0.82723(10) 0.0346 1.0000 Uani . .
C2 C 0.48379(13) 0.2974(3) 0.86796(14) 0.0304 1.0000 Uani . .
C3 C 0.43252(15) 0.2122(4) 0.84896(16) 0.0398 1.0000 Uani . .
C4 C 0.39829(15) 0.1285(4) 0.89113(18) 0.0439 1.0000 Uani . .
C5 C 0.41455(16) 0.1262(4) 0.95455(17) 0.0429 1.0000 Uani . .
Cl6 Cl 0.37122(5) 0.01837(14) 1.00818(5) 0.0634 1.0000 Uani . .
C7 C 0.46356(15) 0.2071(4) 0.97559(16) 0.0415 1.0000 Uani . .
C8 C 0.49939(13) 0.2933(4) 0.93343(14) 0.0336 1.0000 Uani . .
C9 C 0.55155(14) 0.3733(4) 0.95962(15) 0.0373 1.0000 Uani . .
N10 N 0.59600(12) 0.4301(3) 0.92956(12) 0.0344 1.0000 Uani . .
C11 C 0.64662(16) 0.4967(5) 0.96550(16) 0.0448 1.0000 Uani . .
C12 C 0.70318(16) 0.4015(5) 0.95365(17) 0.0460 1.0000 Uani . .
C13 C 0.73763(15) 0.4423(5) 0.89393(17) 0.0488 1.0000 Uani . .
N14 N 0.69809(11) 0.4741(3) 0.83899(12) 0.0364 1.0000 Uani . .
C15 C 0.72146(14) 0.5578(4) 0.79555(15) 0.0397 1.0000 Uani . .
C16 C 0.69497(14) 0.6069(4) 0.73623(14) 0.0345 1.0000 Uani . .
C17 C 0.73288(14) 0.6962(4) 0.69725(15) 0.0390 1.0000 Uani . .
C18 C 0.71289(15) 0.7501(4) 0.64061(15) 0.0371 1.0000 Uani . .
Cl19 Cl 0.76130(5) 0.85667(12) 0.59207(5) 0.0562 1.0000 Uani . .
C20 C 0.65375(15) 0.7194(4) 0.62088(15) 0.0384 1.0000 Uani . .
C21 C 0.61594(14) 0.6329(4) 0.65798(15) 0.0358 1.0000 Uani . .
C22 C 0.63469(13) 0.5740(4) 0.71687(14) 0.0313 1.0000 Uani . .
O23 O 0.59668(10) 0.4918(3) 0.75147(10) 0.0366 1.0000 Uani . .
Zn1 Zn 0.5000 0.50070(6) 0.7500 0.0275 1.0000 Uani S T
Zn2 Zn 0.610202(15) 0.38992(4) 0.834948(16) 0.0309 1.0000 Uani . .
H31 H 0.4217 0.2110 0.8074 0.0480 1.0000 Uiso R .
H41 H 0.3642 0.0742 0.8773 0.0527 1.0000 Uiso R .
H71 H 0.4735 0.2051 1.0186 0.0500 1.0000 Uiso R .
H91 H 0.5528 0.3840 1.0029 0.0448 1.0000 Uiso R .
H112 H 0.6364 0.4968 1.0104 0.0542 1.0000 Uiso R .
H111 H 0.6530 0.6034 0.9513 0.0536 1.0000 Uiso R .
H121 H 0.7298 0.4154 0.9893 0.0552 1.0000 Uiso R .
H122 H 0.6923 0.2919 0.9518 0.0548 1.0000 Uiso R .
H132 H 0.7616 0.5365 0.9023 0.0593 1.0000 Uiso R .
H131 H 0.7648 0.3578 0.8839 0.0593 1.0000 Uiso R .
H151 H 0.7613 0.5942 0.8025 0.0481 1.0000 Uiso R .
H171 H 0.7721 0.7166 0.7105 0.0468 1.0000 Uiso R .
H201 H 0.6395 0.7594 0.5826 0.0459 1.0000 Uiso R .
H211 H 0.5773 0.6125 0.6443 0.0431 1.0000 Uiso R .
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Cl 0.1484 0.1585 11.4604 0.0104 7.1964 1.1662 6.2556 18.5194 1.6455 47.7784
-9.5574 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Zn 0.2839 1.4301 14.0743 3.2655 7.0318 0.2333 5.1652 10.3163 2.4100 58.7097
1.3041 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C42 . N41 Zn2 . 155.1(4) yes
N41 . C42 N43 . 166.8(6) yes
C42 . N43 C44 . 122.0(7) yes
C42 . N43 C46 . 123.1(10) yes
C44 . N43 C46 . 41.1(8) yes
Zn1 1_545 N45 C44 . 144.4(7) yes
N43 . C44 N45 . 161.4(12) yes
N43 . C46 N47 . 168.6(19) yes
C2 . O1 Zn1 . 135.85(18) yes
C2 . O1 Zn2 . 121.52(18) yes
Zn1 . O1 Zn2 . 102.62(9) yes
O1 . C2 C3 . 121.5(3) yes
O1 . C2 C8 . 121.1(3) yes
C3 . C2 C8 . 117.3(3) yes
C2 . C3 C4 . 121.9(3) yes
C2 . C3 H31 . 119.5 no
C4 . C3 H31 . 118.6 no
C3 . C4 C5 . 119.6(3) yes
C3 . C4 H41 . 120.1 no
C5 . C4 H41 . 120.3 no
C4 . C5 Cl6 . 119.6(3) yes
C4 . C5 C7 . 121.0(3) yes
Cl6 . C5 C7 . 119.4(3) yes
C5 . C7 C8 . 120.5(3) yes
C5 . C7 H71 . 119.8 no
C8 . C7 H71 . 119.7 no
C2 . C8 C7 . 119.6(3) yes
C2 . C8 C9 . 123.4(3) yes
C7 . C8 C9 . 116.9(3) yes
C8 . C9 N10 . 127.1(3) yes
C8 . C9 H91 . 116.8 no
N10 . C9 H91 . 116.1 no
C9 . N10 C11 . 118.6(3) yes
C9 . N10 Zn2 . 122.9(2) yes
C11 . N10 Zn2 . 117.0(2) yes
N10 . C11 C12 . 109.4(3) yes
N10 . C11 H112 . 109.3 no
C12 . C11 H112 . 110.6 no
N10 . C11 H111 . 108.4 no
C12 . C11 H111 . 109.7 no
H112 . C11 H111 . 109.4 no
C11 . C12 C13 . 115.3(3) yes
C11 . C12 H121 . 107.8 no
C13 . C12 H121 . 108.7 no
C11 . C12 H122 . 109.0 no
C13 . C12 H122 . 108.3 no
H121 . C12 H122 . 107.5 no
C12 . C13 N14 . 113.8(3) yes
C12 . C13 H132 . 108.1 no
N14 . C13 H132 . 108.0 no
C12 . C13 H131 . 108.8 no
N14 . C13 H131 . 109.4 no
H132 . C13 H131 . 108.8 no
C13 . N14 C15 . 115.6(3) yes
C13 . N14 Zn2 . 121.4(2) yes
C15 . N14 Zn2 . 123.0(2) yes
N14 . C15 C16 . 128.8(3) yes
N14 . C15 H151 . 116.7 no
C16 . C15 H151 . 114.6 no
C15 . C16 C17 . 115.4(3) yes
C15 . C16 C22 . 124.8(3) yes
C17 . C16 C22 . 119.8(3) yes
C16 . C17 C18 . 120.8(3) yes
C16 . C17 H171 . 118.8 no
C18 . C17 H171 . 120.5 no
C17 . C18 Cl19 . 120.0(3) yes
C17 . C18 C20 . 120.2(3) yes
Cl19 . C18 C20 . 119.7(3) yes
C18 . C20 C21 . 120.1(3) yes
C18 . C20 H201 . 120.3 no
C21 . C20 H201 . 119.6 no
C20 . C21 C22 . 121.7(3) yes
C20 . C21 H211 . 119.3 no
C22 . C21 H211 . 119.0 no
C16 . C22 C21 . 117.4(3) yes
C16 . C22 O23 . 122.8(3) yes
C21 . C22 O23 . 119.8(3) yes
C22 . O23 Zn1 . 127.5(2) yes
C22 . O23 Zn2 . 129.18(19) yes
Zn1 . O23 Zn2 . 100.26(9) yes
O23 . Zn1 O23 4_656 175.89(13) yes
O23 . Zn1 N45 4_666 102.2(2) yes
O23 4_656 Zn1 N45 4_666 81.7(2) yes
O23 . Zn1 N45 1_565 81.7(2) yes
O23 4_656 Zn1 N45 1_565 102.2(2) yes
N45 4_666 Zn1 N45 1_565 43.6(4) yes
O23 . Zn1 O1 . 77.61(8) yes
O23 4_656 Zn1 O1 . 100.15(9) yes
N45 4_666 Zn1 O1 . 143.1(2) yes
N45 1_565 Zn1 O1 . 101.2(2) yes
O23 . Zn1 O1 4_656 100.15(9) yes
O23 4_656 Zn1 O1 4_656 77.61(8) yes
N45 4_666 Zn1 O1 4_656 101.2(2) yes
N45 1_565 Zn1 O1 4_656 143.1(2) yes
O1 . Zn1 O1 4_656 115.30(14) yes
O1 . Zn2 N14 . 162.60(11) yes
O1 . Zn2 N10 . 86.22(9) yes
N14 . Zn2 N10 . 92.52(10) yes
O1 . Zn2 N41 . 93.87(12) yes
N14 . Zn2 N41 . 103.09(13) yes
N10 . Zn2 N41 . 106.57(13) yes
O1 . Zn2 O23 . 78.75(8) yes
N14 . Zn2 O23 . 91.40(9) yes
N10 . Zn2 O23 . 140.14(11) yes
N41 . Zn2 O23 . 111.07(12) yes
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
N41 C42 . 1.102(6) yes
N41 Zn2 . 2.034(4) yes
C42 N43 . 1.300(7) yes
N43 C44 . 1.305(2) yes
N43 C46 . 1.297(2) yes
N45 Zn1 1_545 2.015(6) yes
N45 C44 . 1.300(9) yes
C46 N47 . 1.066(10) yes
O1 C2 . 1.314(3) yes
O1 Zn1 . 1.983(2) yes
O1 Zn2 . 2.077(2) yes
C2 C3 . 1.404(4) yes
C2 C8 . 1.429(4) yes
C3 C4 . 1.372(5) yes
C3 H31 . 0.912 no
C4 C5 . 1.390(5) yes
C4 H41 . 0.932 no
C5 Cl6 . 1.748(3) yes
C5 C7 . 1.359(5) yes
C7 C8 . 1.403(4) yes
C7 H71 . 0.937 no
C8 C9 . 1.450(4) yes
C9 N10 . 1.266(4) yes
C9 H91 . 0.922 no
N10 C11 . 1.467(4) yes
N10 Zn2 . 2.057(3) yes
C11 C12 . 1.512(5) yes
C11 H112 . 0.977 no
C11 H111 . 0.972 no
C12 C13 . 1.516(5) yes
C12 H121 . 0.964 no
C12 H122 . 0.970 no
C13 N14 . 1.479(4) yes
C13 H132 . 0.981 no
C13 H131 . 0.964 no
N14 C15 . 1.275(4) yes
N14 Zn2 . 2.070(3) yes
C15 C16 . 1.448(4) yes
C15 H151 . 0.945 no
C16 C17 . 1.402(4) yes
C16 C22 . 1.420(4) yes
C17 C18 . 1.359(5) yes
C17 H171 . 0.926 no
C18 Cl19 . 1.741(3) yes
C18 C20 . 1.395(5) yes
C20 C21 . 1.364(4) yes
C20 H201 . 0.935 no
C21 C22 . 1.407(4) yes
C21 H211 . 0.918 no
C22 O23 . 1.317(3) yes
O23 Zn1 . 2.134(2) yes
O23 Zn2 . 1.994(2) yes
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_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C7 H71 N47 2_657 158.7(3) 0.937 2.445 3.335(6) yes
C21 H211 N47 4_666 145.2(3) 0.918 2.532 3.328(6) yes
