#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/68/4506807.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_4506807
loop_
_publ_author_name
'Wang, Yu-Ling'
'Fu, Jiang-Hong'
'Wei, Jia-Jia'
'Xu, Xiang'
'Li, Xin-Fa'
'Liu, Qing-Yan'
_publ_section_title
;
 Noncentrosymmetric Organic Solid and Its Zinc Coordination Polymer with
 Diamonded Network Prepared from an Ionothermal Reaction: Syntheses,
 Crystal Structures, and Second-Order Nonlinear Optics Properties
;
_journal_issue                   9
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              4663
_journal_paper_doi               10.1021/cg300889x
_journal_volume                  12
_journal_year                    2012
_chemical_formula_sum            'C18 H12 N6 O4 Zn'
_chemical_formula_weight         441.71
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 115.5500(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.4567(16)
_cell_length_b                   20.188(3)
_cell_length_c                   8.1381(10)
_cell_measurement_reflns_used    4503
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.86
_cell_measurement_theta_min      2.77
_cell_volume                     1846.4(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0239
_diffrn_reflns_av_sigmaI/netI    0.0461
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            8434
_diffrn_reflns_theta_full        28.34
_diffrn_reflns_theta_max         28.34
_diffrn_reflns_theta_min         2.77
_exptl_absorpt_coefficient_mu    1.370
_exptl_absorpt_correction_T_max  0.6761
_exptl_absorpt_correction_T_min  0.5970
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker 2008)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.589
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.31
_refine_diff_density_max         0.435
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.009(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         4116
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.0347
_refine_ls_R_factor_gt           0.0291
_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)+(0.0359P)²+0.0817P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0687
_refine_ls_wR_factor_ref         0.0716
_reflns_number_gt                3750
_reflns_number_total             4116
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg300889x_si_001.cif
_cod_data_source_block           Zn(tzbc)2
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from
2011-04-26.

'_exptl_absorpt_correction_type' value 'Multi-scan'
changed to 'multi-scan' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_Hall     C-2yc
_cod_original_sg_symbol_H-M      Cc
_cod_database_code               4506807
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -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
_atom_site_refinement_flags
Zn1 Zn 0.41219(3) 0.384128(11) 0.30638(4) 0.02662(8) Uani 1 1 d .
O1 O 0.5670(2) 0.42106(11) 0.3796(4) 0.0529(6) Uani 1 1 d .
O2 O 0.5326(2) 0.52764(13) 0.3268(5) 0.0785(10) Uani 1 1 d .
O3 O 0.85623(18) 0.14845(10) 1.5587(3) 0.0402(5) Uani 1 1 d .
O4 O 0.7461(2) 0.21922(15) 1.6250(3) 0.0666(8) Uani 1 1 d .
N1 N 1.1028(2) 0.51830(11) 0.7197(3) 0.0356(6) Uani 1 1 d .
N2 N 1.1776(2) 0.47214(14) 0.8352(5) 0.0656(10) Uani 1 1 d .
N3 N 1.27921(19) 0.55782(11) 0.8014(3) 0.0306(5) Uani 1 1 d .
N4 N 0.5486(2) 0.26764(11) 0.7703(3) 0.0352(5) Uani 1 1 d .
N5 N 0.4997(3) 0.21749(11) 0.6490(3) 0.0488(7) Uani 1 1 d .
N6 N 0.4598(2) 0.31587(10) 0.5075(3) 0.0335(5) Uani 1 1 d .
C1 C 0.7333(3) 0.49032(15) 0.4734(5) 0.0399(7) Uani 1 1 d .
C2 C 0.8099(3) 0.43810(16) 0.5235(8) 0.0906(18) Uani 1 1 d .
H2B H 0.7791 0.3953 0.5012 0.109 Uiso 1 1 calc R
C3 C 0.9304(4) 0.44644(19) 0.6053(9) 0.092(2) Uani 1 1 d .
H3A H 0.9806 0.4098 0.6387 0.111 Uiso 1 1 calc R
C4 C 0.9763(2) 0.50842(14) 0.6376(4) 0.0377(6) Uani 1 1 d .
C5 C 0.9034(4) 0.5602(2) 0.5955(9) 0.093(2) Uani 1 1 d .
H5A H 0.9351 0.6027 0.6197 0.111 Uiso 1 1 calc R
C6 C 0.7814(3) 0.55190(17) 0.5164(8) 0.0875(17) Uani 1 1 d .
H6A H 0.7319 0.5887 0.4923 0.105 Uiso 1 1 calc R
C7 C 0.5996(3) 0.48064(14) 0.3845(4) 0.0412(7) Uani 1 1 d .
C8 C 1.2825(3) 0.49788(18) 0.8790(5) 0.0547(9) Uani 1 1 d .
H8A H 1.3529 0.4771 0.9561 0.066 Uiso 1 1 calc R
C9 C 1.1659(2) 0.56798(14) 0.7011(4) 0.0364(6) Uani 1 1 d .
H9A H 1.1342 0.6048 0.6273 0.044 Uiso 1 1 calc R
C10 C 0.7267(3) 0.21698(14) 1.3205(4) 0.0349(6) Uani 1 1 d .
C11 C 0.6573(3) 0.27380(14) 1.2694(4) 0.0418(7) Uani 1 1 d .
H11A H 0.6485 0.2995 1.3577 0.050 Uiso 1 1 calc R
C12 C 0.6009(3) 0.29254(16) 1.0886(4) 0.0401(8) Uani 1 1 d .
H12A H 0.5559 0.3312 1.0547 0.048 Uiso 1 1 calc R
C13 C 0.6126(2) 0.25327(13) 0.9602(4) 0.0347(6) Uani 1 1 d .
C14 C 0.6862(3) 0.19779(17) 1.0096(5) 0.0461(9) Uani 1 1 d .
H14A H 0.6972 0.1730 0.9217 0.055 Uiso 1 1 calc R
C15 C 0.7423(3) 0.18027(14) 1.1899(4) 0.0427(7) Uani 1 1 d .
H15A H 0.7914 0.1432 1.2243 0.051 Uiso 1 1 calc R
C16 C 0.7800(3) 0.19404(15) 1.5168(4) 0.0399(6) Uani 1 1 d .
C17 C 0.4479(3) 0.24840(13) 0.4943(4) 0.0473(8) Uani 1 1 d .
H17A H 0.4065 0.2266 0.3842 0.057 Uiso 1 1 calc R
C18 C 0.5240(2) 0.32592(12) 0.6834(4) 0.0323(5) Uani 1 1 d .
H18A H 0.5484 0.3671 0.7384 0.039 Uiso 1 1 calc R
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'
B B 0.0013 0.0007 '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'
F F 0.0171 0.0103 '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
O1 Zn1 O3 108.57(10) . 4_453
O1 Zn1 N3 119.38(9) . 2_464
O3 Zn1 N3 104.60(9) 4_453 2_464
O1 Zn1 N6 96.29(11) . .
O3 Zn1 N6 117.26(10) 4_453 .
N3 Zn1 N6 111.34(10) 2_464 .
C7 O1 Zn1 130.5(2) . .
C16 O3 Zn1 114.8(2) . 4_556
C9 N1 N2 109.5(2) . .
C9 N1 C4 129.7(2) . .
N2 N1 C4 120.7(2) . .
C8 N2 N1 102.8(2) . .
C9 N3 C8 103.8(2) . .
C9 N3 Zn1 125.35(18) . 2_665
C8 N3 Zn1 130.5(2) . 2_665
C18 N4 N5 110.0(2) . .
C18 N4 C13 130.0(2) . .
N5 N4 C13 120.0(2) . .
C17 N5 N4 103.0(2) . .
C18 N6 C17 103.4(2) . .
C18 N6 Zn1 126.99(18) . .
C17 N6 Zn1 129.06(19) . .
C6 C1 C2 117.2(3) . .
C6 C1 C7 120.8(3) . .
C2 C1 C7 121.8(3) . .
C1 C2 C3 122.1(3) . .
C1 C2 H2B 118.9 . .
C3 C2 H2B 118.9 . .
C4 C3 C2 119.5(3) . .
C4 C3 H3A 120.2 . .
C2 C3 H3A 120.2 . .
C5 C4 C3 119.5(3) . .
C5 C4 N1 120.1(3) . .
C3 C4 N1 120.4(3) . .
C4 C5 C6 121.1(3) . .
C4 C5 H5A 119.4 . .
C6 C5 H5A 119.4 . .
C1 C6 C5 120.3(3) . .
C1 C6 H6A 119.8 . .
C5 C6 H6A 119.8 . .
O2 C7 O1 124.9(3) . .
O2 C7 C1 120.9(3) . .
O1 C7 C1 114.2(3) . .
N2 C8 N3 113.7(3) . .
N2 C8 H8A 123.1 . .
N3 C8 H8A 123.1 . .
N3 C9 N1 110.2(2) . .
N3 C9 H9A 124.9 . .
N1 C9 H9A 124.9 . .
C15 C10 C11 119.4(3) . .
C15 C10 C16 120.4(3) . .
C11 C10 C16 120.2(3) . .
C12 C11 C10 120.6(3) . .
C12 C11 H11A 119.7 . .
C10 C11 H11A 119.7 . .
C13 C12 C11 118.8(3) . .
C13 C12 H12A 120.6 . .
C11 C12 H12A 120.6 . .
C12 C13 C14 121.3(3) . .
C12 C13 N4 120.9(2) . .
C14 C13 N4 117.8(3) . .
C15 C14 C13 119.0(3) . .
C15 C14 H14A 120.5 . .
C13 C14 H14A 120.5 . .
C14 C15 C10 120.7(3) . .
C14 C15 H15A 119.6 . .
C10 C15 H15A 119.6 . .
O4 C16 O3 123.8(3) . .
O4 C16 C10 119.7(3) . .
O3 C16 C10 116.5(3) . .
N5 C17 N6 114.2(3) . .
N5 C17 H17A 122.9 . .
N6 C17 H17A 122.9 . .
N6 C18 N4 109.4(2) . .
N6 C18 H18A 125.3 . .
N4 C18 H18A 125.3 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Zn1 O1 1.908(2) .
Zn1 O3 1.9418(19) 4_453
Zn1 N3 2.015(2) 2_464
Zn1 N6 2.023(2) .
O1 C7 1.265(3) .
O2 C7 1.216(4) .
O3 C16 1.259(4) .
O3 Zn1 1.9418(19) 4_556
O4 C16 1.238(4) .
N1 C9 1.322(4) .
N1 N2 1.366(3) .
N1 C4 1.436(3) .
N2 C8 1.305(4) .
N3 C9 1.307(4) .
N3 C8 1.357(4) .
N3 Zn1 2.015(2) 2_665
N4 C18 1.338(3) .
N4 N5 1.361(3) .
N4 C13 1.430(3) .
N5 C17 1.300(4) .
N6 C18 1.320(3) .
N6 C17 1.369(3) .
C1 C6 1.359(4) .
C1 C2 1.361(5) .
C1 C7 1.516(4) .
C2 C3 1.364(5) .
C2 H2B 0.9300 .
C3 C4 1.354(5) .
C3 H3A 0.9300 .
C4 C5 1.329(5) .
C5 C6 1.381(5) .
C5 H5A 0.9300 .
C6 H6A 0.9300 .
C8 H8A 0.9300 .
C9 H9A 0.9300 .
C10 C15 1.377(4) .
C10 C11 1.388(4) .
C10 C16 1.514(4) .
C11 C12 1.382(4) .
C11 H11A 0.9300 .
C12 C13 1.369(4) .
C12 H12A 0.9300 .
C13 C14 1.392(4) .
C14 C15 1.372(4) .
C14 H14A 0.9300 .
C15 H15A 0.9300 .
C17 H17A 0.9300 .
C18 H18A 0.9300 .
