#------------------------------------------------------------------------------
#$Date: 2023-11-10 04:20:50 +0200 (Fri, 10 Nov 2023) $
#$Revision: 287507 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/76/7247699.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_7247699
loop_
_publ_author_name
'Zheng, Yongpeng'
'Li, Jianxiao'
'Qi, Chaorong'
'Wu, Wanqing'
'Jiang, Huanfeng'
_publ_section_title
;
 Rapid assembly of structurally diverse cyanamides and disulfanes via
 base-mediated aminoalkylation of aryl thiourea
;
_journal_issue                   47
_journal_name_full               'RSC Advances'
_journal_page_first              33047
_journal_page_last               33052
_journal_paper_doi               10.1039/D3RA06051A
_journal_volume                  13
_journal_year                    2023
_chemical_formula_moiety         'C16 H14 N2 O2'
_chemical_formula_sum            'C16 H14 N2 O2'
_chemical_formula_weight         266.29
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-12-04
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2023-02-14 deposited with the CCDC.	2023-10-31 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.913(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.5729(5)
_cell_length_b                   29.957(2)
_cell_length_c                   6.9575(5)
_cell_measurement_reflns_used    2523
_cell_measurement_temperature    170
_cell_measurement_theta_max      26.032
_cell_measurement_theta_min      2.720
_cell_volume                     1345.19(17)
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_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      170.0
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0670
_diffrn_reflns_av_unetI/netI     0.0628
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            10375
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.357
_diffrn_reflns_theta_min         2.720
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5390
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1326 before and 0.0670 after correction. The Ratio of minimum to maximum transmission is 0.7231. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_description       block
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.200
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2743
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0923
_refine_ls_R_factor_gt           0.0505
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0478P)²+0.2512P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1056
_refine_ls_wR_factor_ref         0.1288
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1819
_reflns_number_total             2743
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ra06051a2.cif
_cod_data_source_block           124z1085112_0m
_cod_database_code               7247699
_shelx_shelxl_version_number     2018/3
_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   0.996
_shelx_estimated_absorpt_t_min   0.989
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C7(H7A,H7B), C16(H16A,H16B)
2.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C15(H15), C6(H6), C2(H2), C5(H5), C3(H3), C4(H4)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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 0.6341(2) 0.61773(4) 0.3798(2) 0.0375(4) Uani 1 1 d . . . . .
O1 O 0.89980(19) 0.56582(4) 0.4447(2) 0.0370(4) Uani 1 1 d . . . . .
N1 N 0.4467(2) 0.44103(5) 0.1960(2) 0.0279(4) Uani 1 1 d . . . . .
N2 N 0.0909(3) 0.41708(6) 0.0442(3) 0.0425(5) Uani 1 1 d . . . . .
C10 C 0.4872(3) 0.48720(6) 0.2384(2) 0.0248(4) Uani 1 1 d . . . . .
C11 C 0.3268(3) 0.51799(6) 0.1988(3) 0.0278(4) Uani 1 1 d . . . . .
H11 H 0.190909 0.508171 0.143306 0.033 Uiso 1 1 calc R . . . .
C8 C 0.6134(3) 0.40729(6) 0.2402(3) 0.0280(4) Uani 1 1 d . . . . .
H8A H 0.671591 0.407821 0.382291 0.034 Uiso 1 1 calc R . . . .
H8B H 0.725932 0.415149 0.169801 0.034 Uiso 1 1 calc R . . . .
C9 C 0.2559(3) 0.42822(6) 0.1146(3) 0.0304(5) Uani 1 1 d . . . . .
C12 C 0.3631(3) 0.56328(6) 0.2398(3) 0.0292(4) Uani 1 1 d . . . . .
H12 H 0.254208 0.584568 0.213534 0.035 Uiso 1 1 calc R . . . .
C15 C 0.6899(3) 0.50033(6) 0.3193(3) 0.0281(4) Uani 1 1 d . . . . .
H15 H 0.800752 0.479519 0.345969 0.034 Uiso 1 1 calc R . . . .
C14 C 0.7188(3) 0.54496(6) 0.3576(2) 0.0274(4) Uani 1 1 d . . . . .
C13 C 0.5605(3) 0.57572(6) 0.3189(3) 0.0277(4) Uani 1 1 d . . . . .
C7 C 0.5365(3) 0.36027(6) 0.1816(3) 0.0359(5) Uani 1 1 d . . . . .
H7A H 0.422011 0.352244 0.249254 0.043 Uiso 1 1 calc R . . . .
H7B H 0.483527 0.358997 0.038664 0.043 Uiso 1 1 calc R . . . .
C1 C 0.7137(3) 0.32777(6) 0.2372(3) 0.0372(5) Uani 1 1 d . . . . .
C16 C 0.8552(3) 0.61266(6) 0.4282(3) 0.0378(5) Uani 1 1 d . . . . .
H16A H 0.920352 0.626044 0.324626 0.045 Uiso 1 1 calc R . . . .
H16B H 0.910539 0.627872 0.553465 0.045 Uiso 1 1 calc R . . . .
C6 C 0.8532(3) 0.32150(7) 0.1132(4) 0.0462(6) Uani 1 1 d . . . . .
H6 H 0.831339 0.336400 -0.009564 0.055 Uiso 1 1 calc R . . . .
C2 C 0.7461(4) 0.30564(8) 0.4148(4) 0.0525(6) Uani 1 1 d . . . . .
H2 H 0.651661 0.309413 0.501320 0.063 Uiso 1 1 calc R . . . .
C5 C 1.0233(4) 0.29404(8) 0.1646(5) 0.0652(8) Uani 1 1 d . . . . .
H5 H 1.117768 0.290180 0.078132 0.078 Uiso 1 1 calc R . . . .
C3 C 0.9176(4) 0.27782(8) 0.4667(5) 0.0722(9) Uani 1 1 d . . . . .
H3 H 0.939560 0.262599 0.588689 0.087 Uiso 1 1 calc R . . . .
C4 C 1.0554(4) 0.27227(8) 0.3420(6) 0.0783(10) Uani 1 1 d . . . . .
H4 H 1.172512 0.253408 0.378484 0.094 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C13 O2 C16 104.76(14) . . ?
C14 O1 C16 105.19(14) . . ?
C10 N1 C8 121.12(14) . . ?
C9 N1 C10 119.37(15) . . ?
C9 N1 C8 119.50(15) . . ?
C11 C10 N1 119.84(16) . . ?
C11 C10 C15 121.45(17) . . ?
C15 C10 N1 118.71(16) . . ?
C10 C11 H11 119.6 . . ?
C10 C11 C12 120.70(17) . . ?
C12 C11 H11 119.6 . . ?
N1 C8 H8A 109.1 . . ?
N1 C8 H8B 109.1 . . ?
N1 C8 C7 112.35(15) . . ?
H8A C8 H8B 107.9 . . ?
C7 C8 H8A 109.1 . . ?
C7 C8 H8B 109.1 . . ?
N2 C9 N1 179.9(3) . . ?
C11 C12 H12 121.3 . . ?
C13 C12 C11 117.45(17) . . ?
C13 C12 H12 121.3 . . ?
C10 C15 H15 122.0 . . ?
C14 C15 C10 116.01(17) . . ?
C14 C15 H15 122.0 . . ?
C15 C14 O1 127.19(17) . . ?
C15 C14 C13 122.90(17) . . ?
C13 C14 O1 109.86(16) . . ?
C12 C13 O2 128.53(17) . . ?
C12 C13 C14 121.50(17) . . ?
C14 C13 O2 109.92(16) . . ?
C8 C7 H7A 109.9 . . ?
C8 C7 H7B 109.9 . . ?
H7A C7 H7B 108.3 . . ?
C1 C7 C8 109.03(15) . . ?
C1 C7 H7A 109.9 . . ?
C1 C7 H7B 109.9 . . ?
C6 C1 C7 119.76(19) . . ?
C2 C1 C7 121.3(2) . . ?
C2 C1 C6 118.9(2) . . ?
O2 C16 H16A 110.2 . . ?
O2 C16 H16B 110.2 . . ?
O1 C16 O2 107.76(14) . . ?
O1 C16 H16A 110.2 . . ?
O1 C16 H16B 110.2 . . ?
H16A C16 H16B 108.5 . . ?
C1 C6 H6 119.4 . . ?
C5 C6 C1 121.2(2) . . ?
C5 C6 H6 119.4 . . ?
C1 C2 H2 120.0 . . ?
C1 C2 C3 119.9(3) . . ?
C3 C2 H2 120.0 . . ?
C6 C5 H5 120.2 . . ?
C4 C5 C6 119.6(3) . . ?
C4 C5 H5 120.2 . . ?
C2 C3 H3 119.8 . . ?
C4 C3 C2 120.3(3) . . ?
C4 C3 H3 119.8 . . ?
C5 C4 C3 120.0(2) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
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 C13 1.385(2) . ?
O2 C16 1.436(2) . ?
O1 C14 1.378(2) . ?
O1 C16 1.434(2) . ?
N1 C10 1.429(2) . ?
N1 C8 1.480(2) . ?
N1 C9 1.331(2) . ?
N2 C9 1.152(2) . ?
C10 C11 1.389(2) . ?
C10 C15 1.402(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.397(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C7 1.526(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.362(3) . ?
C15 H15 0.9500 . ?
C15 C14 1.369(3) . ?
C14 C13 1.378(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C1 1.511(3) . ?
C1 C6 1.386(3) . ?
C1 C2 1.383(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C6 H6 0.9500 . ?
C6 C5 1.380(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.393(3) . ?
C5 H5 0.9500 . ?
C5 C4 1.377(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.378(4) . ?
C4 H4 0.9500 . ?
