#------------------------------------------------------------------------------
#$Date: 2019-11-03 13:04:48 +0200 (Sun, 03 Nov 2019) $
#$Revision: 221482 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/12/83/4128359.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_4128359
loop_
_publ_author_name
'Lu, Jing'
'Lian, Yu-Kun'
'Xiong, Lin'
'Wu, Qian-Ru'
'Zhao, Min'
'Shi, Ke-Xin'
'Chen, Ling'
'Wu, Li-Ming'
_publ_section_title
;
 How To Maximize Birefringence and Nonlinearity of π-Conjugated
 Cyanurates.
;
_journal_issue                   40
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              16151
_journal_page_last               16159
_journal_paper_doi               10.1021/jacs.9b08851
_journal_volume                  141
_journal_year                    2019
_chemical_formula_sum            'C3 H5 Li2 N3 O5'
_chemical_formula_weight         176.98
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90.92(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   3.4142(18)
_cell_length_b                   16.974(11)
_cell_length_c                   11.176(8)
_cell_measurement_reflns_used    2524
_cell_measurement_temperature    88(2)
_cell_measurement_theta_max      27.08
_cell_measurement_theta_min      3.01
_cell_volume                     647.6(7)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      88(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0912
_diffrn_reflns_av_unetI/netI     0.0459
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11527
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.425
_diffrn_reflns_theta_min         3.014
_exptl_absorpt_coefficient_mu    0.163
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.815
_exptl_crystal_description       strip
_exptl_crystal_F_000             360
_exptl_transmission_factor_max   0.7456
_exptl_transmission_factor_min   0.6496
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         1467
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0587
_refine_ls_R_factor_gt           0.0403
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0478P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0807
_refine_ls_wR_factor_ref         0.0865
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1135
_reflns_number_total             1467
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            Li2HC3N3O3-2H2O.cif
_cod_data_source_block           Li2HC3N3O3_2H2O
_cod_database_code               4128359
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
O1 O 0.4866(3) 0.44198(5) 0.86896(9) 0.0236(3) Uani 1 1 d
H1 H -0.026(7) 0.2967(12) 0.937(2) 0.054(7) Uiso 1 1 d
N1 N 0.2735(4) 0.56720(7) 0.88237(12) 0.0185(3) Uani 1 1 d
O2 O -0.0194(3) 0.29030(6) 0.86154(11) 0.0223(3) Uani 1 1 d
H2 H -0.035(6) 0.2395(15) 0.8450(19) 0.057(6) Uiso 1 1 d
N2 N 0.1000(4) 0.63956(6) 0.71301(11) 0.0179(3) Uani 1 1 d
O003 O 0.1910(3) 0.58009(6) 0.53426(9) 0.0223(3) Uani 1 1 d
H3 H 0.601(9) 0.3113(16) 0.599(3) 0.085(10) Uiso 1 1 d
O3 O 0.4039(4) 0.31924(6) 0.63454(10) 0.0249(3) Uani 1 1 d
N3 N 0.3251(3) 0.50624(6) 0.69633(11) 0.0182(3) Uani 1 1 d
O004 O 0.0476(3) 0.69150(6) 0.89900(10) 0.0236(3) Uani 1 1 d
H4 H 0.248(9) 0.2781(16) 0.637(2) 0.088(9) Uiso 1 1 d
C009 C 0.2053(4) 0.57564(8) 0.64789(13) 0.0162(3) Uani 1 1 d
H5 H 0.317(5) 0.5637(10) 0.9599(19) 0.033(5) Uiso 1 1 d
C00A C 0.1355(4) 0.63500(7) 0.83118(13) 0.0162(3) Uani 1 1 d
C00B C 0.3654(4) 0.50225(7) 0.81505(13) 0.0167(3) Uani 1 1 d
Li0C Li 0.4767(8) 0.33874(14) 0.8070(2) 0.0258(6) Uani 1 1 d
Li0D Li 0.6897(8) 0.57277(15) 0.4426(2) 0.0277(6) Uani 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 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Li Li -0.0003 0.0001 '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'
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
C00B O1 Li0C 125.32(13) . .
C00A N1 C00B 121.81(14) . .
C00A N1 H5 121.4(11) . .
C00B N1 H5 116.7(11) . .
Li0C O2 Li0C 118.10(14) . 1_455
Li0C O2 H1 106.8(16) . .
Li0C O2 H1 102.3(16) 1_455 .
Li0C O2 H2 112.9(15) . .
Li0C O2 H2 106.8(14) 1_455 .
H1 O2 H2 109.3(19) . .
C00A N2 C009 117.78(12) . .
C009 O003 Li0D 122.04(12) . 1_455
C009 O003 Li0D 119.16(13) . .
Li0D O003 Li0D 117.68(15) 1_455 .
C009 O003 Li0D 80.81(9) . 3_666
Li0D O003 Li0D 96.87(10) 1_455 3_666
Li0D O003 Li0D 81.85(10) . 3_666
Li0C O3 Li0D 106.14(12) . 3_666
Li0C O3 H3 115(2) . .
Li0D O3 H3 94(2) 3_666 .
Li0C O3 H4 99.8(18) . .
Li0D O3 H4 129.4(18) 3_666 .
H3 O3 H4 113(3) . .
C00B N3 C009 117.82(12) . .
C00B N3 Li0D 136.11(12) . 3_666
C009 N3 Li0D 105.19(13) . 3_666
O003 C009 N3 117.14(12) . .
O003 C009 N2 118.77(12) . .
N3 C009 N2 124.09(13) . .
O003 C009 Li0D 71.91(10) . 3_666
N3 C009 Li0D 46.26(10) . 3_666
N2 C009 Li0D 165.81(11) . 3_666
O004 C00A N2 122.33(13) . .
O004 C00A N1 118.22(14) . .
N2 C00A N1 119.45(12) . .
O1 C00B N3 123.19(13) . .
O1 C00B N1 117.91(14) . .
N3 C00B N1 118.90(12) . .
O1 Li0C O3 121.19(14) . .
O1 Li0C O2 106.38(14) . .
O3 Li0C O2 97.83(13) . .
O1 Li0C O2 105.12(13) . 1_655
O3 Li0C O2 108.98(14) . 1_655
O2 Li0C O2 118.10(14) . 1_655
O1 Li0C Li0D 83.46(11) . 3_666
O3 Li0C Li0D 37.80(8) . 3_666
O2 Li0C Li0D 108.69(12) . 3_666
O2 Li0C Li0D 126.77(13) 1_655 3_666
O1 Li0C Li0C 90.68(9) . 1_455
O3 Li0C Li0C 83.65(9) . 1_455
O2 Li0C Li0C 31.00(8) . 1_455
O2 Li0C Li0C 149.10(8) 1_655 1_455
Li0D Li0C Li0C 80.62(7) 3_666 1_455
O1 Li0C Li0C 89.32(9) . 1_655
O3 Li0C Li0C 96.35(9) . 1_655
O2 Li0C Li0C 149.00(8) . 1_655
O2 Li0C Li0C 30.90(8) 1_655 1_655
Li0D Li0C Li0C 99.38(7) 3_666 1_655
Li0C Li0C Li0C 180.0 1_455 1_655
O1 Li0C H4 136.7(7) . .
O3 Li0C H4 22.2(7) . .
O2 Li0C H4 77.7(8) . .
O2 Li0C H4 110.5(7) 1_655 .
Li0D Li0C H4 55.7(7) 3_666 .
Li0C Li0C H4 70.9(8) 1_455 .
Li0C Li0C H4 109.1(8) 1_655 .
O003 Li0D O003 117.68(15) 1_655 .
O003 Li0D O3 106.78(13) 1_655 3_666
O003 Li0D O3 91.81(12) . 3_666
O003 Li0D N3 116.24(14) 1_655 3_666
O003 Li0D N3 114.61(14) . 3_666
O3 Li0D N3 105.36(14) 3_666 3_666
O003 Li0D O003 83.13(10) 1_655 3_666
O003 Li0D O003 98.15(10) . 3_666
O3 Li0D O003 160.75(14) 3_666 3_666
N3 Li0D O003 55.48(8) 3_666 3_666
O003 Li0D C009 97.53(11) 1_655 3_666
O003 Li0D C009 111.27(11) . 3_666
O3 Li0D C009 133.47(14) 3_666 3_666
N3 Li0D C009 28.55(6) 3_666 3_666
O003 Li0D C009 27.28(5) 3_666 3_666
O003 Li0D Li0D 101.54(15) 1_655 3_666
O003 Li0D Li0D 58.01(10) . 3_666
O3 Li0D Li0D 146.04(18) 3_666 3_666
N3 Li0D Li0D 77.62(12) 3_666 3_666
O003 Li0D Li0D 40.14(8) 3_666 3_666
C009 Li0D Li0D 58.31(10) 3_666 3_666
O003 Li0D Li0C 123.94(13) 1_655 3_666
O003 Li0D Li0C 105.97(13) . 3_666
O3 Li0D Li0C 36.06(7) 3_666 3_666
N3 Li0D Li0C 69.31(11) 3_666 3_666
O003 Li0D Li0C 124.77(11) 3_666 3_666
C009 Li0D Li0C 97.59(10) 3_666 3_666
Li0D Li0D Li0C 131.90(15) 3_666 3_666
O003 Li0D Li0D 31.34(9) 1_655 1_655
O003 Li0D Li0D 149.02(9) . 1_655
O3 Li0D Li0D 98.58(9) 3_666 1_655
N3 Li0D Li0D 90.71(8) 3_666 1_655
O003 Li0D Li0D 81.21(6) 3_666 1_655
C009 Li0D Li0D 82.14(7) 3_666 1_655
Li0D Li0D Li0D 115.30(11) 3_666 1_655
Li0C Li0D Li0D 99.38(7) 3_666 1_655
O003 Li0D Li0D 148.66(9) 1_655 1_455
O003 Li0D Li0D 30.98(9) . 1_455
O3 Li0D Li0D 81.42(9) 3_666 1_455
N3 Li0D Li0D 89.29(8) 3_666 1_455
O003 Li0D Li0D 98.79(6) 3_666 1_455
C009 Li0D Li0D 97.86(6) 3_666 1_455
Li0D Li0D Li0D 64.70(11) 3_666 1_455
Li0C Li0D Li0D 80.62(7) 3_666 1_455
Li0D Li0D Li0D 180.0 1_655 1_455
O003 Li0D Li0D 48.71(8) 1_655 3_766
O003 Li0D Li0D 111.82(14) . 3_766
O3 Li0D Li0D 151.50(16) 3_666 3_766
N3 Li0D Li0D 79.79(12) 3_666 3_766
O003 Li0D Li0D 34.41(6) 3_666 3_766
C009 Li0D Li0D 53.27(8) 3_666 3_766
Li0D Li0D Li0D 62.30(11) 3_666 3_766
Li0C Li0D Li0D 138.55(14) 3_666 3_766
Li0D Li0D Li0D 53.00(9) 1_655 3_766
Li0D Li0D Li0D 127.00(9) 1_455 3_766
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C00B 1.2541(17) .
O1 Li0C 1.884(3) .
N1 C00A 1.3655(19) .
N1 C00B 1.3740(19) .
N1 H5 0.88(2) .
O2 Li0C 1.988(3) .
O2 Li0C 1.993(3) 1_455
O2 H1 0.85(2) .
O2 H2 0.88(3) .
N2 C00A 1.327(2) .
N2 C009 1.3581(18) .
O003 C009 1.2723(19) .
O003 Li0D 1.984(3) 1_455
O003 Li0D 2.005(3) .
O003 Li0D 2.638(3) 3_666
O3 Li0C 1.967(3) .
O3 Li0D 2.048(3) 3_666
O3 H3 0.79(3) .
O3 H4 0.88(3) .
N3 C00B 1.333(2) .
N3 C009 1.3569(19) .
N3 Li0D 2.051(3) 3_666
O004 C00A 1.2617(17) .
C009 Li0D 2.740(3) 3_666
Li0C O2 1.994(3) 1_655
Li0C Li0D 3.210(4) 3_666
Li0C Li0C 3.4142(18) 1_455
Li0C Li0C 3.4142(18) 1_655
Li0C H4 2.29(3) .
Li0D O003 1.984(3) 1_655
Li0D O3 2.048(3) 3_666
Li0D N3 2.051(3) 3_666
Li0D O003 2.639(3) 3_666
Li0D C009 2.740(3) 3_666
Li0D Li0D 3.079(5) 3_666
Li0D Li0C 3.210(4) 3_666
Li0D Li0D 3.4142(18) 1_655
Li0D Li0D 3.4142(18) 1_455
Li0D Li0D 3.486(6) 3_766
