#------------------------------------------------------------------------------
#$Date: 2020-09-05 04:28:58 +0300 (Sat, 05 Sep 2020) $
#$Revision: 255910 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/11/7241184.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_7241184
loop_
_publ_author_name
'Gao, Mingxiao'
'Zhang, Xinyuan'
'Guo, Yangwu'
'Yao, Jiyong'
'Zhang, Guochun'
'Hu, Zhanggui'
'Wu, Yicheng'
_publ_section_title
;
 Rational Structure Design of Isoxazolone-based Crystals with Large
 Second-Order Optical Nonlinearity
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D0CE01100B
_journal_year                    2020
_chemical_formula_moiety         'C24 H17 N O3'
_chemical_formula_sum            'C24 H17 N O3'
_chemical_formula_weight         367.38
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_audit_creation_date             2019-07-15
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2020-06-02 deposited with the CCDC.	2020-09-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.2990(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   26.8338(4)
_cell_length_b                   5.81950(10)
_cell_length_c                   11.9509(2)
_cell_measurement_reflns_used    8502
_cell_measurement_temperature    296.7(4)
_cell_measurement_theta_max      79.0080
_cell_measurement_theta_min      7.5550
_cell_volume                     1808.43(5)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      296.7(4)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0250
_diffrn_reflns_av_unetI/netI     0.0228
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10427
_diffrn_reflns_point_group_measured_fraction_full 0.824
_diffrn_reflns_point_group_measured_fraction_max 0.792
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         79.407
_diffrn_reflns_theta_min         3.399
_exptl_absorpt_coefficient_mu    0.720
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_description       prism
_exptl_crystal_F_000             768
_refine_diff_density_max         0.125
_refine_diff_density_min         -0.089
_refine_diff_density_rms         0.028
_refine_ls_abs_structure_details
;
 Flack x determined using 1112 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(9)
_refine_ls_extinction_coef       0.0021(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/4 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     322
_refine_ls_number_reflns         3110
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0285
_refine_ls_R_factor_gt           0.0283
_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)+(0.0519P)²+0.1398P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0820
_refine_ls_wR_factor_ref         0.0824
_reflns_Friedel_coverage         0.601
_reflns_Friedel_fraction_full    0.649
_reflns_Friedel_fraction_max     0.595
_reflns_number_gt                3057
_reflns_number_total             3110
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ce01100b2.cif
_cod_data_source_block           C24H17NO3
_cod_database_code               7241184
_shelx_shelxl_version_number     2016/4
_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.
;
_olex2_refinement_description
;
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O 0.44886(6) 1.2856(3) 0.27776(14) 0.0638(4) Uani 1 1 d . . . . .
O3 O 0.30021(6) 1.0519(3) 0.74060(14) 0.0652(4) Uani 1 1 d . . . . .
O1 O 0.51046(7) 1.0464(3) 0.25564(15) 0.0727(5) Uani 1 1 d . . . . .
N1 N 0.41291(7) 1.3068(3) 0.34949(17) 0.0601(4) Uani 1 1 d . . . . .
C4 C 0.48023(7) 0.8059(3) 0.47441(15) 0.0472(4) Uani 1 1 d . . . . .
C3 C 0.42092(7) 1.1343(3) 0.41965(17) 0.0478(4) Uani 1 1 d . . . . .
C21 C 0.32936(7) 1.0575(3) 0.66168(17) 0.0504(4) Uani 1 1 d . . . . .
C5 C 0.52120(7) 0.6403(3) 0.48086(16) 0.0473(4) Uani 1 1 d . . . . .
C18 C 0.38974(7) 1.1071(3) 0.50456(16) 0.0469(4) Uani 1 1 d . . . . .
C6 C 0.52690(7) 0.4744(3) 0.56901(18) 0.0519(4) Uani 1 1 d . . . . .
C2 C 0.46197(7) 0.9855(3) 0.40357(16) 0.0467(4) Uani 1 1 d . . . . .
C1 C 0.47821(8) 1.0931(3) 0.30744(18) 0.0547(4) Uani 1 1 d . . . . .
C8 C 0.59682(7) 0.3037(3) 0.51074(17) 0.0506(4) Uani 1 1 d . . . . .
C7 C 0.56388(8) 0.3048(4) 0.58403(18) 0.0545(4) Uani 1 1 d . . . . .
C16 C 0.59223(7) 0.4668(3) 0.42346(17) 0.0526(4) Uani 1 1 d . . . . .
C23 C 0.36162(8) 0.9073(3) 0.50702(18) 0.0526(4) Uani 1 1 d . . . . .
C19 C 0.38775(7) 1.2804(3) 0.58366(19) 0.0535(4) Uani 1 1 d . . . . .
C14 C 0.66303(9) 0.2278(4) 0.4218(2) 0.0630(5) Uani 1 1 d . . . . .
C9 C 0.64066(8) 0.1543(4) 0.50951(18) 0.0567(5) Uani 1 1 d . . . . .
C22 C 0.33124(8) 0.8823(3) 0.58452(19) 0.0541(4) Uani 1 1 d . . . . .
C17 C 0.55469(8) 0.6348(3) 0.40691(17) 0.0531(4) Uani 1 1 d . . . . .
C10 C 0.66098(11) -0.0301(4) 0.5804(3) 0.0735(6) Uani 1 1 d . . . . .
C15 C 0.63299(10) 0.4287(5) 0.3577(2) 0.0687(6) Uani 1 1 d . . . . .
C20 C 0.35811(8) 1.2556(3) 0.66202(19) 0.0560(5) Uani 1 1 d . . . . .
C11 C 0.70487(12) -0.1334(5) 0.5625(3) 0.0847(8) Uani 1 1 d . . . . .
C12 C 0.72784(11) -0.0577(6) 0.4776(3) 0.0826(8) Uani 1 1 d . . . . .
C13 C 0.70711(10) 0.1216(6) 0.4056(2) 0.0757(7) Uani 1 1 d . . . . .
C24 C 0.27270(14) 0.8488(6) 0.7484(4) 0.0841(8) Uani 1 1 d . . . . .
H17 H 0.5516(10) 0.747(4) 0.350(2) 0.055(5) Uiso 1 1 d . . . . .
H4 H 0.4626(8) 0.781(4) 0.538(2) 0.049(5) Uiso 1 1 d . . . . .
H20 H 0.3572(10) 1.380(5) 0.714(2) 0.066(7) Uiso 1 1 d . . . . .
H23 H 0.3637(10) 0.785(4) 0.454(2) 0.059(6) Uiso 1 1 d . . . . .
H10 H 0.6446(12) -0.083(6) 0.645(3) 0.085(9) Uiso 1 1 d . . . . .
H7 H 0.5664(11) 0.188(5) 0.644(3) 0.073(8) Uiso 1 1 d . . . . .
H22 H 0.3120(11) 0.744(5) 0.589(3) 0.071(7) Uiso 1 1 d . . . . .
H24A H 0.2457(14) 0.819(6) 0.676(3) 0.088(10) Uiso 1 1 d . . . . .
H19 H 0.4092(10) 1.422(5) 0.582(2) 0.064(7) Uiso 1 1 d . . . . .
H24B H 0.2534(14) 0.886(6) 0.807(3) 0.095(10) Uiso 1 1 d . . . . .
H12 H 0.7569(14) -0.138(6) 0.466(3) 0.091(9) Uiso 1 1 d . . . . .
H24C H 0.2944(14) 0.722(7) 0.768(3) 0.101(11) Uiso 1 1 d . . . . .
H15A H 0.6166(14) 0.383(6) 0.277(3) 0.094(10) Uiso 1 1 d . . . . .
H15B H 0.6547(15) 0.576(7) 0.366(4) 0.111(12) Uiso 1 1 d . . . . .
H13 H 0.7230(13) 0.179(6) 0.337(3) 0.091(10) Uiso 1 1 d . . . . .
H11 H 0.7170(17) -0.257(8) 0.608(4) 0.119(14) Uiso 1 1 d . . . . .
H6 H 0.5060(11) 0.485(5) 0.623(2) 0.068(7) Uiso 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 0.0181 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
_geom_angle_publ_flag
C1 O2 N1 110.05(14) . . ?
C21 O3 C24 117.7(2) . . ?
C3 N1 O2 106.86(15) . . ?
C5 C4 H4 110.8(13) . . ?
C2 C4 C5 134.18(17) . . ?
C2 C4 H4 115.0(13) . . ?
N1 C3 C18 119.89(16) . . ?
N1 C3 C2 112.84(17) . . ?
C2 C3 C18 127.27(16) . . ?
O3 C21 C22 124.32(17) . . ?
O3 C21 C20 115.50(17) . . ?
C22 C21 C20 120.17(18) . . ?
C6 C5 C4 115.85(17) . . ?
C17 C5 C4 125.10(17) . . ?
C17 C5 C6 119.05(17) . . ?
C23 C18 C3 120.50(16) . . ?
C23 C18 C19 118.65(18) . . ?
C19 C18 C3 120.85(16) . . ?
C5 C6 H6 119.0(16) . . ?
C7 C6 C5 121.95(19) . . ?
C7 C6 H6 118.9(17) . . ?
C4 C2 C3 123.07(17) . . ?
C4 C2 C1 133.31(17) . . ?
C3 C2 C1 103.36(16) . . ?
O2 C1 C2 106.87(17) . . ?
O1 C1 O2 119.36(18) . . ?
O1 C1 C2 133.77(19) . . ?
C7 C8 C16 121.10(17) . . ?
C7 C8 C9 130.25(18) . . ?
C16 C8 C9 108.62(18) . . ?
C6 C7 C8 118.06(18) . . ?
C6 C7 H7 120.7(17) . . ?
C8 C7 H7 121.2(17) . . ?
C8 C16 C15 110.34(18) . . ?
C17 C16 C8 121.04(18) . . ?
C17 C16 C15 128.62(19) . . ?
C18 C23 H23 119.0(15) . . ?
C22 C23 C18 120.95(17) . . ?
C22 C23 H23 120.0(15) . . ?
C18 C19 H19 117.7(15) . . ?
C20 C19 C18 120.73(17) . . ?
C20 C19 H19 121.6(15) . . ?
C9 C14 C15 109.97(18) . . ?
C13 C14 C9 120.4(2) . . ?
C13 C14 C15 129.6(3) . . ?
C14 C9 C8 108.70(18) . . ?
C10 C9 C8 130.2(2) . . ?
C10 C9 C14 121.1(2) . . ?
C21 C22 C23 119.53(17) . . ?
C21 C22 H22 117.9(18) . . ?
C23 C22 H22 122.5(18) . . ?
C5 C17 H17 119.3(15) . . ?
C16 C17 C5 118.79(18) . . ?
C16 C17 H17 121.9(16) . . ?
C9 C10 H10 120.8(18) . . ?
C11 C10 C9 117.4(3) . . ?
C11 C10 H10 121.7(18) . . ?
C16 C15 C14 102.30(19) . . ?
C16 C15 H15A 110(2) . . ?
C16 C15 H15B 107(2) . . ?
C14 C15 H15A 110(2) . . ?
C14 C15 H15B 112(2) . . ?
H15A C15 H15B 115(3) . . ?
C21 C20 H20 121.9(16) . . ?
C19 C20 C21 119.94(17) . . ?
C19 C20 H20 118.1(16) . . ?
C10 C11 H11 116(3) . . ?
C12 C11 C10 121.7(3) . . ?
C12 C11 H11 122(2) . . ?
C11 C12 H12 119(2) . . ?
C13 C12 C11 121.0(2) . . ?
C13 C12 H12 120(2) . . ?
C14 C13 H13 119.0(18) . . ?
C12 C13 C14 118.3(3) . . ?
C12 C13 H13 122.6(18) . . ?
O3 C24 H24A 112(2) . . ?
O3 C24 H24B 104(2) . . ?
O3 C24 H24C 112(2) . . ?
H24A C24 H24B 105(3) . . ?
H24A C24 H24C 111(3) . . ?
H24B C24 H24C 114(3) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 N1 1.445(2) . ?
O2 C1 1.365(2) . ?
O3 C21 1.366(2) . ?
O3 C24 1.409(4) . ?
O1 C1 1.213(3) . ?
N1 C3 1.292(3) . ?
C4 C5 1.449(2) . ?
C4 C2 1.358(3) . ?
C4 H4 1.00(2) . ?
C3 C18 1.475(3) . ?
C3 C2 1.451(2) . ?
C21 C22 1.384(3) . ?
C21 C20 1.387(3) . ?
C5 C6 1.409(3) . ?
C5 C17 1.408(3) . ?
C18 C23 1.390(2) . ?
C18 C19 1.392(3) . ?
C6 C7 1.380(3) . ?
C6 H6 0.95(3) . ?
C2 C1 1.466(3) . ?
C8 C7 1.390(3) . ?
C8 C16 1.393(3) . ?
C8 C9 1.466(3) . ?
C7 H7 0.97(3) . ?
C16 C17 1.383(3) . ?
C16 C15 1.512(3) . ?
C23 C22 1.384(3) . ?
C23 H23 0.96(3) . ?
C19 C20 1.378(3) . ?
C19 H19 1.01(3) . ?
C14 C9 1.397(3) . ?
C14 C15 1.516(3) . ?
C14 C13 1.390(3) . ?
C9 C10 1.393(3) . ?
C22 H22 0.96(3) . ?
C17 H17 0.93(3) . ?
C10 C11 1.385(4) . ?
C10 H10 1.03(3) . ?
C15 H15A 1.00(4) . ?
C15 H15B 1.03(4) . ?
C20 H20 0.96(3) . ?
C11 C12 1.383(5) . ?
C11 H11 0.91(5) . ?
C12 C13 1.380(4) . ?
C12 H12 0.95(4) . ?
C13 H13 1.07(3) . ?
C24 H24A 1.00(4) . ?
C24 H24B 0.99(4) . ?
C24 H24C 0.94(4) . ?
