#------------------------------------------------------------------------------
#$Date: 2019-09-18 03:45:37 +0300 (Wed, 18 Sep 2019) $
#$Revision: 218405 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/39/7233914.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_7233914
loop_
_publ_author_name
'Li, Zhonghua'
'Jia, Lina'
'Shi, Peng'
'Jiang, Shuang'
'Gong, Junbo'
'Wu, Songgu'
_publ_section_title
;
 Versatile solid forms of boscalid: insight into the crystal structures
 and phase transformations
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/C9CE00306A
_journal_year                    2019
_chemical_formula_moiety         'C18 H12 Cl2 N2 O, C2 H4 O'
_chemical_formula_sum            'C20 H16 Cl2 N2 O2'
_chemical_formula_weight         387.25
_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   geom
_audit_creation_date             2017-07-12
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2019-03-03 deposited with the CCDC.    2019-09-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.21(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.284(3)
_cell_length_b                   20.468(4)
_cell_length_c                   7.4983(15)
_cell_measurement_reflns_used    7119
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.56
_cell_measurement_theta_min      3.20
_cell_volume                     1874.2(7)
_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    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.957
_diffrn_measurement_device_type  'RIGAKU R-AXIS RAPID IP'
_diffrn_measurement_method       'Rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0666
_diffrn_reflns_av_unetI/netI     0.0617
_diffrn_reflns_Laue_measured_fraction_full 0.970
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            16514
_diffrn_reflns_point_group_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.479
_diffrn_reflns_theta_min         3.202
_exptl_absorpt_coefficient_mu    0.363
_exptl_absorpt_correction_T_max  0.9476
_exptl_absorpt_correction_T_min  0.9148
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS; Bruker, 2000'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.241
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       0.0089(10)
_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   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         4112
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.1253
_refine_ls_R_factor_gt           0.0660
_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)+(0.0263P)²+1.2657P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1016
_refine_ls_wR_factor_ref         0.1243
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2477
_reflns_number_total             4112
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9ce00306a2.cif
_cod_data_source_block           b_CCDC3
_cod_original_cell_volume        1874.3(7)
_cod_database_code               7233914
_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.
;
_shelx_estimated_absorpt_t_max   0.948
_shelx_estimated_absorpt_t_min   0.915
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B), C20(H20A,H20B)
2.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C1(H1), C5(H5), C8(H8), C2(H2), C10(H10), C18(H18), C4(H4), C9(H9),
 C17(H17), C16(H16), N1(H21)
;
_olex2_submission_special_instructions 'No special instructions were received'
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
_atom_site_refinement_flags_posn
Cl2 Cl 0.24457(8) 0.09230(5) 0.08083(11) 0.0743(3) Uani 1 1 d .
Cl1 Cl 0.47795(8) -0.15275(5) 1.04839(11) 0.0793(3) Uani 1 1 d .
C6 C 0.2587(2) -0.14496(13) 0.5244(4) 0.0445(7) Uani 1 1 d .
C14 C 0.1578(2) 0.08493(13) 0.3966(4) 0.0443(7) Uani 1 1 d .
C7 C 0.1829(2) -0.14821(14) 0.3554(4) 0.0461(7) Uani 1 1 d .
C12 C 0.1340(2) -0.09295(14) 0.2695(4) 0.0426(7) Uani 1 1 d .
C13 C 0.0993(2) 0.02318(14) 0.3320(3) 0.0448(7) Uani 1 1 d .
C11 C 0.0608(2) -0.09982(16) 0.1162(4) 0.0548(8) Uani 1 1 d .
H11 H 0.030477 -0.062952 0.057667 0.066 Uiso 1 1 calc R
C1 C 0.2273(2) -0.11434(14) 0.6768(4) 0.0517(8) Uani 1 1 d .
H1 H 0.160895 -0.092203 0.670554 0.062 Uiso 1 1 calc R
C5 C 0.3587(2) -0.17756(14) 0.5383(4) 0.0511(7) Uani 1 1 d .
H5 H 0.380381 -0.198563 0.438014 0.061 Uiso 1 1 calc R
C8 C 0.1548(3) -0.20940(15) 0.2809(4) 0.0556(8) Uani 1 1 d .
H8 H 0.188382 -0.246589 0.332556 0.067 Uiso 1 1 calc R
C2 C 0.2943(3) -0.11669(15) 0.8375(4) 0.0557(8) Uani 1 1 d .
H2 H 0.272919 -0.096392 0.939008 0.067 Uiso 1 1 calc R
C10 C 0.0329(3) -0.16104(18) 0.0505(4) 0.0643(9) Uani 1 1 d .
H10 H -0.017465 -0.165367 -0.050666 0.077 Uiso 1 1 calc R
C18 C 0.1424(3) 0.11128(16) 0.5621(4) 0.0616(9) Uani 1 1 d .
H18 H 0.098571 0.089645 0.636783 0.074 Uiso 1 1 calc R
C3 C 0.3930(3) -0.14928(15) 0.8461(4) 0.0535(8) Uani 1 1 d .
C15 C 0.2243(3) 0.12068(15) 0.2943(4) 0.0530(8) Uani 1 1 d .
C4 C 0.4265(3) -0.17944(14) 0.6978(4) 0.0544(8) Uani 1 1 d .
H4 H 0.493686 -0.200754 0.704596 0.065 Uiso 1 1 calc R
C9 C 0.0790(3) -0.21593(18) 0.1336(4) 0.0633(9) Uani 1 1 d .
H9 H 0.058885 -0.257229 0.090010 0.076 Uiso 1 1 calc R
C17 C 0.1916(3) 0.16927(18) 0.6162(5) 0.0769(11) Uani 1 1 d .
H17 H 0.181375 0.187497 0.726812 0.092 Uiso 1 1 calc R
C16 C 0.2555(3) 0.19934(18) 0.5041(6) 0.0773(11) Uani 1 1 d .
H16 H 0.289320 0.238345 0.541991 0.093 Uiso 1 1 calc R
C19 C 0.4645(3) 0.00011(19) 1.3186(5) 0.0785(11) Uani 1 1 d .
H19A H 0.481139 0.044476 1.285047 0.094 Uiso 1 1 calc R
H19B H 0.433102 -0.022648 1.211781 0.094 Uiso 1 1 calc R
C20 C 0.4329(3) 0.0334(2) 1.6063(5) 0.0864(12) Uani 1 1 d .
H20A H 0.380361 0.032920 1.694052 0.104 Uiso 1 1 calc R
H20B H 0.448658 0.078554 1.579568 0.104 Uiso 1 1 calc R
O1 O 0.00148(17) 0.02270(10) 0.2860(3) 0.0583(6) Uani 1 1 d .
O2 O 0.38789(18) 0.00119(12) 1.4475(4) 0.0781(7) Uani 1 1 d .
N2 N 0.2730(2) 0.17628(14) 0.3421(4) 0.0673(8) Uani 1 1 d .
N1 N 0.16552(19) -0.02986(11) 0.3343(3) 0.0472(6) Uani 1 1 d .
H21 H 0.232489 -0.024836 0.378808 0.057 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'
Cl Cl 0.1484 0.1585 '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
C1 C6 C7 120.9(3) . .
C5 C6 C7 120.5(2) . .
C5 C6 C1 118.3(3) . .
C18 C14 C13 120.5(3) . .
C18 C14 C15 115.8(3) . .
C15 C14 C13 123.6(3) . .
C12 C7 C6 123.4(3) . .
C8 C7 C6 118.9(3) . .
C8 C7 C12 117.6(3) . .
C7 C12 N1 119.3(3) . .
C11 C12 C7 120.3(3) . .
C11 C12 N1 120.3(3) . .
O1 C13 C14 121.4(3) . .
O1 C13 N1 124.8(3) . .
N1 C13 C14 113.8(2) . .
C12 C11 H11 119.9 . .
C10 C11 C12 120.1(3) . .
C10 C11 H11 119.9 . .
C6 C1 H1 119.8 . .
C2 C1 C6 120.4(3) . .
C2 C1 H1 119.8 . .
C6 C5 H5 119.2 . .
C4 C5 C6 121.5(3) . .
C4 C5 H5 119.2 . .
C7 C8 H8 119.2 . .
C9 C8 C7 121.7(3) . .
C9 C8 H8 119.2 . .
C1 C2 H2 120.2 . .
C3 C2 C1 119.6(3) . .
C3 C2 H2 120.2 . .
C11 C10 H10 119.8 . .
C9 C10 C11 120.5(3) . .
C9 C10 H10 119.8 . .
C14 C18 H18 119.9 . .
C17 C18 C14 120.2(3) . .
C17 C18 H18 119.9 . .
C2 C3 Cl1 120.0(2) . .
C4 C3 Cl1 118.8(3) . .
C4 C3 C2 121.2(3) . .
C14 C15 Cl2 118.8(3) . .
N2 C15 Cl2 115.6(2) . .
N2 C15 C14 125.6(3) . .
C5 C4 H4 120.6 . .
C3 C4 C5 118.8(3) . .
C3 C4 H4 120.6 . .
C8 C9 C10 119.7(3) . .
C8 C9 H9 120.2 . .
C10 C9 H9 120.2 . .
C18 C17 H17 120.9 . .
C16 C17 C18 118.3(3) . .
C16 C17 H17 120.9 . .
C17 C16 H16 117.9 . .
N2 C16 C17 124.1(3) . .
N2 C16 H16 117.9 . .
H19A C19 H19B 108.1 . .
C20 C19 H19A 109.6 3_658 .
C20 C19 H19B 109.6 3_658 .
O2 C19 H19A 109.6 . .
O2 C19 H19B 109.6 . .
O2 C19 C20 110.2(3) . 3_658
C19 C20 H20A 109.7 3_658 .
C19 C20 H20B 109.7 3_658 .
H20A C20 H20B 108.2 . .
O2 C20 C19 109.9(3) . 3_658
O2 C20 H20A 109.7 . .
O2 C20 H20B 109.7 . .
C20 O2 C19 110.6(3) . .
C15 N2 C16 116.0(3) . .
C12 N1 H21 117.1 . .
C13 N1 C12 125.7(2) . .
C13 N1 H21 117.1 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl2 C15 1.746(3) .
Cl1 C3 1.747(3) .
C6 C7 1.491(4) .
C6 C1 1.394(4) .
C6 C5 1.391(4) .
C14 C13 1.508(4) .
C14 C18 1.385(4) .
C14 C15 1.388(4) .
C7 C12 1.404(4) .
C7 C8 1.399(4) .
C12 C11 1.388(4) .
C12 N1 1.419(3) .
C13 O1 1.214(3) .
C13 N1 1.355(3) .
C11 H11 0.9300 .
C11 C10 1.376(4) .
C1 H1 0.9300 .
C1 C2 1.384(4) .
C5 H5 0.9300 .
C5 C4 1.382(4) .
C8 H8 0.9300 .
C8 C9 1.372(4) .
C2 H2 0.9300 .
C2 C3 1.378(4) .
C10 H10 0.9300 .
C10 C9 1.376(5) .
C18 H18 0.9300 .
C18 C17 1.373(5) .
C3 C4 1.373(4) .
C15 N2 1.317(4) .
C4 H4 0.9300 .
C9 H9 0.9300 .
C17 H17 0.9300 .
C17 C16 1.359(5) .
C16 H16 0.9300 .
C16 N2 1.342(4) .
C19 H19A 0.9700 .
C19 H19B 0.9700 .
C19 C20 1.490(5) 3_658
C19 O2 1.420(4) .
C20 H20A 0.9700 .
C20 H20B 0.9700 .
C20 O2 1.420(4) .
N1 H21 0.8600 .
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
_geom_torsion_site_symmetry_1
Cl2 C15 N2 C16 178.3(2) .
Cl1 C3 C4 C5 179.1(2) .
C6 C7 C12 C11 -177.5(3) .
C6 C7 C12 N1 6.6(4) .
C6 C7 C8 C9 174.9(3) .
C6 C1 C2 C3 0.3(5) .
C6 C5 C4 C3 1.2(4) .
C14 C13 N1 C12 -175.4(2) .
C14 C18 C17 C16 -0.4(5) .
C14 C15 N2 C16 0.0(5) .
C7 C6 C1 C2 174.2(3) .
C7 C6 C5 C4 -174.9(3) .
C7 C12 C11 C10 2.1(4) .
C7 C12 N1 C13 -146.7(3) .
C7 C8 C9 C10 3.3(5) .
C12 C7 C8 C9 -2.6(4) .
C12 C11 C10 C9 -1.5(5) .
C13 C14 C18 C17 -176.7(3) .
C13 C14 C15 Cl2 -1.5(4) .
C13 C14 C15 N2 176.8(3) .
C11 C12 N1 C13 37.4(4) .
C11 C10 C9 C8 -1.2(5) .
C1 C6 C7 C12 54.9(4) .
C1 C6 C7 C8 -122.5(3) .
C1 C6 C5 C4 -0.6(4) .
C1 C2 C3 Cl1 -179.8(2) .
C1 C2 C3 C4 0.2(5) .
C5 C6 C7 C12 -131.0(3) .
C5 C6 C7 C8 51.7(4) .
C5 C6 C1 C2 -0.1(4) .
C8 C7 C12 C11 -0.1(4) .
C8 C7 C12 N1 -176.0(2) .
C2 C3 C4 C5 -1.0(5) .
C18 C14 C13 O1 71.4(4) .
C18 C14 C13 N1 -107.4(3) .
C18 C14 C15 Cl2 -178.0(2) .
C18 C14 C15 N2 0.3(5) .
C18 C17 C16 N2 0.7(6) .
C15 C14 C13 O1 -104.9(3) .
C15 C14 C13 N1 76.2(3) .
C15 C14 C18 C17 -0.1(5) .
C17 C16 N2 C15 -0.5(5) .
C19 C20 O2 C19 -58.1(4) 3_658
C20 C19 O2 C20 58.3(4) 3_658
O1 C13 N1 C12 5.7(4) .
N1 C12 C11 C10 178.0(3) .
