#------------------------------------------------------------------------------
#$Date: 2025-08-22 18:52:37 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301865 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/49/7224953.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_7224953
loop_
_publ_author_name
'Zhang, Xinyuan'
'Jiang, Xingxing'
'Liu, Pengxiang'
'Li, Yin'
'Tu, Heng'
'Lin, Zheshuai'
'Xu, Degang'
'Zhang, Guochun'
'Wu, Yicheng'
'Yao, Jianquan'
_publ_section_title
;
 Molecular design on isoxazolone-based derivatives with large second-order
 harmonic generation effect and terahertz wave generation
;
_journal_issue                   20
_journal_name_full               CrystEngComm
_journal_page_first              3667
_journal_paper_doi               10.1039/C6CE00398B
_journal_volume                  18
_journal_year                    2016
_chemical_formula_sum            'C18 H15 N O4'
_chemical_formula_weight         309.31
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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_creation_method           SHELXL-97
_audit_update_record
;
2016-01-19 deposited with the CCDC.
2016-04-19 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 104.306(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.339(2)
_cell_length_b                   19.964(6)
_cell_length_c                   10.771(3)
_cell_measurement_reflns_used    6031
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      31.497
_cell_measurement_theta_min      2.202
_cell_volume                     1529.2(8)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      153(2)
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  AFC10/Saturn724+
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0362
_diffrn_reflns_av_sigmaI/netI    0.0335
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            18224
_diffrn_reflns_theta_full        31.49
_diffrn_reflns_theta_max         31.49
_diffrn_reflns_theta_min         3.04
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.308
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       0.0074(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         5029
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.0664
_refine_ls_R_factor_gt           0.0578
_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)+(0.0610P)²+0.6900P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1331
_refine_ls_wR_factor_ref         0.1400
_reflns_number_gt                4516
_reflns_number_total             5029
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6ce00398b2.cif
_cod_data_source_block           bo3034
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 

 Adding full bibliography for 7224953--7224955.cif.
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7224953
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
_atom_site_refinement_flags
O1 O 0.31181(15) 0.46936(5) 0.09646(9) 0.0293(2) Uani 1 1 d .
O2 O 0.24373(16) 0.55435(5) 0.21221(9) 0.0307(2) Uani 1 1 d .
O3 O 0.13589(14) 0.61455(5) 0.78501(9) 0.0260(2) Uani 1 1 d .
O4 O 0.10126(15) 0.65763(5) 0.55594(9) 0.0300(2) Uani 1 1 d .
N1 N 0.34674(18) 0.39839(6) 0.11027(11) 0.0291(3) Uani 1 1 d .
C1 C 0.28218(18) 0.46296(6) 0.64145(12) 0.0238(2) Uani 1 1 d .
H1 H 0.3215 0.4182 0.6631 0.029 Uiso 1 1 calc R
C2 C 0.24216(19) 0.50444(6) 0.73489(12) 0.0239(2) Uani 1 1 d .
H2 H 0.2556 0.4883 0.8196 0.029 Uiso 1 1 calc R
C3 C 0.18231(17) 0.56982(6) 0.70351(11) 0.0218(2) Uani 1 1 d .
C4 C 0.16523(18) 0.59347(6) 0.57685(12) 0.0218(2) Uani 1 1 d .
C5 C 0.20796(17) 0.55241(6) 0.48511(11) 0.0216(2) Uani 1 1 d .
H5 H 0.1985 0.5690 0.4011 0.026 Uiso 1 1 calc R
C6 C 0.26594(17) 0.48559(6) 0.51615(11) 0.0212(2) Uani 1 1 d .
C7 C 0.30415(17) 0.43725(6) 0.42638(12) 0.0219(2) Uani 1 1 d .
H7 H 0.3371 0.3944 0.4636 0.026 Uiso 1 1 calc R
C8 C 0.28037(19) 0.49543(6) 0.20781(12) 0.0236(2) Uani 1 1 d .
C9 C 0.30325(17) 0.43968(6) 0.29953(11) 0.0210(2) Uani 1 1 d .
C10 C 0.34146(18) 0.38261(6) 0.22607(12) 0.0228(2) Uani 1 1 d .
C11 C 0.37162(19) 0.31215(6) 0.26893(12) 0.0234(2) Uani 1 1 d .
C12 C 0.5231(2) 0.27596(7) 0.24688(14) 0.0301(3) Uani 1 1 d .
H12 H 0.6061 0.2962 0.2028 0.036 Uiso 1 1 calc R
C13 C 0.5524(2) 0.21013(7) 0.28967(15) 0.0334(3) Uani 1 1 d .
H13 H 0.6555 0.1854 0.2746 0.040 Uiso 1 1 calc R
C14 C 0.4316(2) 0.18037(7) 0.35427(13) 0.0301(3) Uani 1 1 d .
H14 H 0.4531 0.1356 0.3843 0.036 Uiso 1 1 calc R
C15 C 0.2795(2) 0.21593(7) 0.37493(14) 0.0308(3) Uani 1 1 d .
H15 H 0.1964 0.1953 0.4185 0.037 Uiso 1 1 calc R
C16 C 0.2481(2) 0.28160(7) 0.33208(13) 0.0275(3) Uani 1 1 d .
H16 H 0.1431 0.3057 0.3456 0.033 Uiso 1 1 calc R
C17 C 0.1610(2) 0.59399(7) 0.91603(12) 0.0294(3) Uani 1 1 d .
H17A H 0.0782 0.5560 0.9200 0.035 Uiso 1 1 calc R
H17B H 0.1299 0.6313 0.9662 0.035 Uiso 1 1 calc R
H17C H 0.2922 0.5807 0.9513 0.035 Uiso 1 1 calc R
C18 C 0.1018(3) 0.68671(8) 0.43563(16) 0.0501(5) Uani 1 1 d .
H18A H 0.2310 0.6886 0.4260 0.060 Uiso 1 1 calc R
H18B H 0.0500 0.7321 0.4313 0.060 Uiso 1 1 calc R
H18C H 0.0247 0.6594 0.3667 0.060 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'
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
C8 O1 N1 110.20(9)
C3 O3 C17 117.17(11)
C4 O4 C18 117.13(11)
C10 N1 O1 106.95(10)
C2 C1 C6 121.53(12)
C2 C1 H1 119.2
C6 C1 H1 119.2
C1 C2 C3 119.57(11)
C1 C2 H2 120.2
C3 C2 H2 120.2
O3 C3 C2 125.18(11)
O3 C3 C4 115.29(11)
C2 C3 C4 119.52(11)
O4 C4 C5 124.77(11)
O4 C4 C3 114.59(11)
C5 C4 C3 120.63(11)
C4 C5 C6 119.98(11)
C4 C5 H5 120.0
C6 C5 H5 120.0
C1 C6 C5 118.75(11)
C1 C6 C7 116.49(11)
C5 C6 C7 124.72(11)
C9 C7 C6 133.91(12)
C9 C7 H7 113.0
C6 C7 H7 113.0
O2 C8 O1 119.20(11)
O2 C8 C9 134.36(12)
O1 C8 C9 106.44(11)
C7 C9 C10 124.26(11)
C7 C9 C8 132.13(11)
C10 C9 C8 103.48(10)
N1 C10 C9 112.89(11)
N1 C10 C11 119.57(11)
C9 C10 C11 127.54(11)
C12 C11 C16 119.73(12)
C12 C11 C10 120.22(12)
C16 C11 C10 120.04(12)
C13 C12 C11 119.81(13)
C13 C12 H12 120.1
C11 C12 H12 120.1
C14 C13 C12 120.30(13)
C14 C13 H13 119.9
C12 C13 H13 119.9
C15 C14 C13 120.03(13)
C15 C14 H14 120.0
C13 C14 H14 120.0
C14 C15 C16 120.23(13)
C14 C15 H15 119.9
C16 C15 H15 119.9
C15 C16 C11 119.88(13)
C15 C16 H16 120.1
C11 C16 H16 120.1
O3 C17 H17A 109.5
O3 C17 H17B 109.5
H17A C17 H17B 109.5
O3 C17 H17C 109.5
H17A C17 H17C 109.5
H17B C17 H17C 109.5
O4 C18 H18A 109.5
O4 C18 H18B 109.5
H18A C18 H18B 109.5
O4 C18 H18C 109.5
H18A C18 H18C 109.5
H18B C18 H18C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C8 1.3782(16)
O1 N1 1.4410(15)
O2 C8 1.2101(16)
O3 C3 1.3534(15)
O3 C17 1.4371(16)
O4 C4 1.3638(15)
O4 C18 1.4208(18)
N1 C10 1.2963(17)
C1 C2 1.3896(18)
C1 C6 1.4001(17)
C1 H1 0.9500
C2 C3 1.3920(18)
C2 H2 0.9500
C3 C4 1.4196(17)
C4 C5 1.3783(17)
C5 C6 1.4150(17)
C5 H5 0.9500
C6 C7 1.4418(17)
C7 C9 1.3655(17)
C7 H7 0.9500
C8 C9 1.4701(17)
C9 C10 1.4534(17)
C10 C11 1.4800(18)
C11 C12 1.3946(19)
C11 C16 1.4001(19)
C12 C13 1.392(2)
C12 H12 0.9500
C13 C14 1.388(2)
C13 H13 0.9500
C14 C15 1.386(2)
C14 H14 0.9500
C15 C16 1.3902(19)
C15 H15 0.9500
C16 H16 0.9500
C17 H17A 0.9800
C17 H17B 0.9800
C17 H17C 0.9800
C18 H18A 0.9800
C18 H18B 0.9800
C18 H18C 0.9800
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
C8 O1 N1 C10 -1.56(15)
C6 C1 C2 C3 0.8(2)
C17 O3 C3 C2 3.83(19)
C17 O3 C3 C4 -176.64(11)
C1 C2 C3 O3 178.74(12)
C1 C2 C3 C4 -0.77(19)
C18 O4 C4 C5 -8.4(2)
C18 O4 C4 C3 172.94(15)
O3 C3 C4 O4 -1.06(16)
C2 C3 C4 O4 178.50(12)
O3 C3 C4 C5 -179.80(11)
C2 C3 C4 C5 -0.24(19)
O4 C4 C5 C6 -177.35(12)
C3 C4 C5 C6 1.25(19)
C2 C1 C6 C5 0.23(19)
C2 C1 C6 C7 -177.66(12)
C4 C5 C6 C1 -1.24(18)
C4 C5 C6 C7 176.46(12)
C1 C6 C7 C9 179.89(14)
C5 C6 C7 C9 2.1(2)
N1 O1 C8 O2 -178.12(12)
N1 O1 C8 C9 2.30(14)
C6 C7 C9 C10 -177.83(13)
C6 C7 C9 C8 7.1(3)
O2 C8 C9 C7 -5.8(3)
O1 C8 C9 C7 173.70(13)
O2 C8 C9 C10 178.40(16)
O1 C8 C9 C10 -2.11(14)
O1 N1 C10 C9 0.10(15)
O1 N1 C10 C11 179.65(11)
C7 C9 C10 N1 -174.99(12)
C8 C9 C10 N1 1.25(15)
C7 C9 C10 C11 5.5(2)
C8 C9 C10 C11 -178.25(13)
N1 C10 C11 C12 48.20(19)
C9 C10 C11 C12 -132.32(14)
N1 C10 C11 C16 -131.92(14)
C9 C10 C11 C16 47.55(19)
C16 C11 C12 C13 -1.1(2)
C10 C11 C12 C13 178.79(13)
C11 C12 C13 C14 -0.1(2)
C12 C13 C14 C15 0.9(2)
C13 C14 C15 C16 -0.5(2)
C14 C15 C16 C11 -0.6(2)
C12 C11 C16 C15 1.4(2)
C10 C11 C16 C15 -178.45(13)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 809304
