#------------------------------------------------------------------------------
#$Date: 2019-11-24 10:00:55 +0200 (Sun, 24 Nov 2019) $
#$Revision: 237555 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/72/7237283.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_7237283
loop_
_publ_author_name
'Tao, Kewen'
'Wu, Zhenyue'
'Han, Shiguo'
'Zhang, Jing'
'Ji, Chengmin'
'Wang, Yuyin'
'Zhang, Weichuan'
'Luo, Junhua'
'Sun, Zhihua'
_publ_section_title
;
 Switchable behaviors of quadratic nonlinear optical properties
 originating from bi-step phase transitions in a molecule-based crystal
;
_journal_issue                   15
_journal_name_full               'Journal of Materials Chemistry C'
_journal_page_first              4150
_journal_paper_doi               10.1039/C8TC00407B
_journal_volume                  6
_journal_year                    2018
_chemical_formula_moiety         'C6 H2 N3 O7, C7 H16 N'
_chemical_formula_sum            'C13 H18 N4 O7'
_chemical_formula_weight         342.31
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_Hall           '-P 2ac 2n'
_space_group_name_H-M_alt        'P n m a'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2018-01-12 deposited with the CCDC.
2018-03-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.2587(3)
_cell_length_b                   6.7913(2)
_cell_length_c                   12.8788(3)
_cell_measurement_reflns_used    2308
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      72.7700
_cell_measurement_theta_min      4.1720
_cell_volume                     1596.98(7)
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0160
_diffrn_reflns_av_unetI/netI     0.0191
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            4977
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         73.194
_diffrn_reflns_theta_min         4.201
_exptl_absorpt_coefficient_mu    1.002
_exptl_crystal_density_diffrn    1.424
_exptl_crystal_F_000             720
_refine_diff_density_max         0.240
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       0.00281(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     162
_refine_ls_number_reflns         1672
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.0728
_refine_ls_R_factor_gt           0.0621
_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)+(0.0100P)²+1.3200P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1029
_refine_ls_wR_factor_ref         0.1076
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1379
_reflns_number_total             1672
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8tc00407b2.cif
_cod_data_source_block           x
_cod_database_code               7237283
_shelx_shelxl_version_number     2016/6
_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+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'-x, y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z-1/2'
'x, -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_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
O1 O 0.35521(11) 0.250000 0.02940(19) 0.0828(8) Uani 1 2 d S T P
O2 O 0.3371(2) 0.3726(8) -0.1727(3) 0.1238(19) Uani 0.5 1 d . . P
O3 O 0.3998(3) 0.1676(11) -0.2589(4) 0.175(4) Uani 0.5 1 d . . P
O4 O 0.69321(14) 0.250000 -0.0193(3) 0.1120(12) Uani 1 2 d S T P
O5 O 0.66221(15) 0.250000 -0.1787(3) 0.1234(13) Uani 1 2 d S T P
O6 O 0.41083(19) 0.1703(7) 0.2178(2) 0.106(2) Uani 0.5 1 d . . P
O7 O 0.5149(2) 0.1840(7) 0.2438(3) 0.101(2) Uani 0.5 1 d . . P
N1 N 0.3891(2) 0.250000 -0.1822(3) 0.0959(12) Uani 1 2 d S T P
N2 N 0.64693(16) 0.250000 -0.0875(3) 0.0824(9) Uani 1 2 d S T P
N3 N 0.46786(17) 0.250000 0.1869(2) 0.0759(9) Uani 1 2 d S T P
C1 C 0.42064(15) 0.250000 0.0045(2) 0.0560(8) Uani 1 2 d S T P
C2 C 0.44521(16) 0.250000 -0.1017(2) 0.0597(8) Uani 1 2 d S T P
C3 C 0.51648(17) 0.250000 -0.1322(3) 0.0616(8) Uani 1 2 d S T P
H3 H 0.528500 0.250000 -0.202379 0.074 Uiso 1 2 calc R U P
C4 C 0.57065(16) 0.250000 -0.0578(3) 0.0598(8) Uani 1 2 d S T P
C5 C 0.55335(16) 0.250000 0.0455(3) 0.0588(8) Uani 1 2 d S T P
H5 H 0.590346 0.250000 0.095129 0.071 Uiso 1 2 calc R U P
C6 C 0.48165(16) 0.250000 0.0757(2) 0.0558(7) Uani 1 2 d S T P
N4 N 0.2440(2) 0.1611(7) 0.1685(3) 0.0793(14) Uani 0.5 1 d D . P
H4A H 0.2765(16) 0.250000 0.140(2) 0.095 Uiso 1 2 d DS U P
H4B H 0.259(2) 0.043(3) 0.197(3) 0.095 Uiso 0.5 1 d D U P
C7 C 0.2524(2) 0.250000 0.2692(3) 0.132(2) Uani 1 2 d DS T P
H7A H 0.299298 0.284900 0.297517 0.197 Uiso 0.5 1 calc R U P
H7B H 0.249153 0.109436 0.262850 0.197 Uiso 0.5 1 calc R U P
H7C H 0.214389 0.296364 0.314537 0.197 Uiso 0.5 1 calc R U P
C8 C 0.17608(18) 0.250000 0.1083(3) 0.0909(15) Uani 1 2 d S T P
H8 H 0.135792 0.250000 0.158843 0.084(11) Uiso 1 2 d R . P
C9 C 0.1725(2) 0.0733(6) 0.0453(3) 0.1341(15) Uani 1 1 d . . .
H9A H 0.175717 -0.042611 0.089028 0.161 Uiso 1 1 calc DR U .
H9B H 0.212958 0.070713 -0.003566 0.161 Uiso 1 1 calc R U .
C10 C 0.1015(3) 0.0748(11) -0.0117(4) 0.214(4) Uani 1 1 d . . .
H10A H 0.098140 -0.041456 -0.055184 0.257 Uiso 1 1 calc R U .
H10B H 0.061411 0.071127 0.037720 0.257 Uiso 1 1 calc R U .
C11 C 0.0953(5) 0.250000 -0.0756(5) 0.256(10) Uani 1 2 d S T P
H11A H 0.048467 0.249999 -0.111125 0.307 Uiso 1 2 calc R U P
H11B H 0.133711 0.250003 -0.127684 0.307 Uiso 1 2 calc R U P
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
N1 O2 O3 45.1(3) . 8_565
N1 O2 O2 49.0(3) . 8_565
O3 O2 O2 80.3(3) 8_565 8_565
O3 O3 N1 60.9(4) 8_565 .
O3 O3 O2 99.7(3) 8_565 8_565
N1 O3 O2 51.2(3) . 8_565
O6 O6 N3 64.1(2) 8_565 .
O7 O7 N3 68.4(2) 8_565 .
O3 N1 O3 58.1(7) 8_565 .
O3 N1 O2 83.7(4) 8_565 .
O3 N1 O2 121.9(4) . .
O3 N1 O2 121.9(4) 8_565 8_565
O3 N1 O2 83.7(4) . 8_565
O2 N1 O2 82.0(5) . 8_565
O3 N1 C2 119.4(4) 8_565 .
O3 N1 C2 119.4(4) . .
O2 N1 C2 117.2(3) . .
O2 N1 C2 117.2(3) 8_565 .
O5 N2 O4 122.7(3) . .
O5 N2 C4 118.8(3) . .
O4 N2 C4 118.5(3) . .
O7 N3 O7 43.3(4) . 8_565
O7 N3 O6 103.9(3) . .
O7 N3 O6 124.2(4) 8_565 .
O7 N3 O6 124.2(4) . 8_565
O7 N3 O6 103.9(3) 8_565 8_565
O6 N3 O6 51.8(4) . 8_565
O7 N3 C6 118.1(3) . .
O7 N3 C6 118.1(3) 8_565 .
O6 N3 C6 117.5(3) . .
O6 N3 C6 117.5(3) 8_565 .
O1 C1 C2 123.2(3) . .
O1 C1 C6 125.5(3) . .
C2 C1 C6 111.3(3) . .
C3 C2 C1 124.9(3) . .
C3 C2 N1 117.9(3) . .
C1 C2 N1 117.2(3) . .
C2 C3 C4 119.1(3) . .
C5 C4 C3 120.7(3) . .
C5 C4 N2 118.8(3) . .
C3 C4 N2 120.5(3) . .
C6 C5 C4 119.9(3) . .
C5 C6 C1 124.0(3) . .
C5 C6 N3 116.5(3) . .
C1 C6 N3 119.5(3) . .
N4 N4 C7 65.2(2) 8_565 .
N4 N4 C8 67.59(18) 8_565 .
C7 N4 C8 111.4(3) . .
N4 C7 N4 49.6(4) 8_565 .
C9 C8 C9 111.7(4) . 8_565
C9 C8 N4 128.7(3) . 8_565
C9 C8 N4 89.7(3) 8_565 8_565
C9 C8 N4 89.7(3) . .
C9 C8 N4 128.7(3) 8_565 .
N4 C8 N4 44.8(4) 8_565 .
C8 C9 C10 108.0(4) . .
C11 C10 C9 110.6(5) . .
C10 C11 C10 110.1(6) . 8_565
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C1 1.237(3) .
O2 N1 1.269(5) .
O2 O3 1.618(6) 8_565
O2 O2 1.666(11) 8_565
O3 O3 1.119(14) 8_565
O3 N1 1.152(5) .
O4 N2 1.219(4) .
O5 N2 1.207(4) .
O6 O6 1.082(9) 8_565
O6 N3 1.239(4) .
O7 O7 0.896(9) 8_565
O7 N3 1.215(4) .
N1 C2 1.457(4) .
N2 C4 1.444(4) .
N3 C6 1.454(4) .
C1 C2 1.440(4) .
C1 C6 1.442(4) .
C2 C3 1.359(4) .
C3 C4 1.377(4) .
C4 C5 1.367(4) .
C5 C6 1.366(4) .
N4 N4 1.207(10) 8_565
N4 C7 1.439(5) .
N4 C8 1.583(5) .
C8 C9 1.450(4) .
C8 C9 1.450(4) 8_565
C9 C10 1.490(6) .
C10 C11 1.452(7) .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N4 H4A O1 0.923(16) 2.02(2) 2.774(4) 137.5(12) .
N4 H4B O2 0.930(19) 2.69(4) 3.196(6) 115(3) 7_656
N4 H4B O5 0.930(19) 2.46(3) 3.278(5) 147(4) 5_655
C7 H7A O6 0.96 2.41 3.016(5) 120.8 .
C7 H7A O6 0.96 2.30 3.016(5) 130.7 8_565
C7 H7B O2 0.96 2.40 3.130(5) 132.7 7_656
C7 H7C O2 0.96 2.44 3.130(5) 128.4 2_565
C8 H8 O7 0.98 2.58 3.534(5) 164.5 6_556
C8 H8 O7 0.98 2.58 3.534(5) 164.5 3_455
C9 H9A O3 0.97 2.54 3.284(6) 133.3 2
