Synthesis of unsymmetrical urea derivatives via one-pot sequential three-component reactions of cyclic 2-diazo-1,3-diketones, carbodiimides, and 1,2-dihaloethanes.
He, Xinwei; Yang, Cheng; Wu, Yinsong; Xie, Mengqing; Li, Ruxue; Duan, Jiahui; Shang, Yongjia; Organic & biomolecular chemistry 18 (2020) 4178–4182; doi:10.1039/d0ob00683a

data_7157510
_publ_section_title
;
 Synthesis of unsymmetrical urea derivatives via one-pot sequential
 three-component reactions of cyclic 2-diazo-1,3-diketones, carbodiimides,
 and 1,2-dihaloethanes.
;
_journal_issue                   22
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4178
_journal_page_last               4182
_journal_paper_doi               10.1039/d0ob00683a
_journal_volume                  18
_journal_year                    2020
_chemical_formula_moiety         'C14 H23 Cl N2 O2'
_chemical_formula_sum            'C14 H23 Cl N2 O2'
_chemical_formula_weight         286.79
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-03-30
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-03-30 deposited with the CCDC.	2020-05-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.003(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.9531(13)
_cell_length_b                   18.3735(17)
_cell_length_c                   12.4880(12)
_cell_measurement_reflns_used    7023
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.614
_cell_measurement_theta_min      2.454
_cell_volume                     3201.5(5)
_computing_cell_refinement       'SAINT v7.34A (Bruker, 200?)'
_computing_data_collection       'SAINT v7.34A (Bruker, 200?)'
_computing_data_reduction        'SAINT v7.34A (Bruker, 200?)'
_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      293.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1008
_diffrn_reflns_av_unetI/netI     0.0660
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            27226
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.474
_diffrn_reflns_theta_min         1.459
_exptl_absorpt_coefficient_mu    0.239
_exptl_absorpt_correction_T_max  0.9515
_exptl_absorpt_correction_T_min  0.9470
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.190
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1232
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.314
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     392
_refine_ls_number_reflns         7192
_refine_ls_number_restraints     55
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.1040
_refine_ls_R_factor_gt           0.0580
_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/[\s^2^(Fo^2^)+(0.0693P)^2^+0.6597P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1420
_refine_ls_wR_factor_ref         0.1678
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4315
_reflns_number_total             7192
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob00683a2.cif
_cod_data_source_block           151209a
_cod_depositor_comments          'Adding full bibliography for 7157510.cif.'
_cod_database_code               7157510
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.951
_shelx_estimated_absorpt_t_min   0.947
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All C(H,H,H,H,H,H) groups
2. Restrained distances
 C2-C1 \\sim C2-C1A
 with sigma of 0.02
 C3-C2 \\sim C3A-C2
 with sigma of 0.02
 C1-C3 \\sim C1A-C3A
 with sigma of 0.02
 C12A-C14 \\sim C14-C12
 with sigma of 0.02
 C13-C12 \\sim C12A-C13
 with sigma of 0.02
 C12-C11 \\sim C12A-C11A
 with sigma of 0.02
 C11-C10 \\sim C11A-C10
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C1A) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
4. Rigid body (RIGU) restrains
 C3, C2, C1
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 C1A, C2, C3A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 C10, C11A, C12A, C14, C13
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
5. Others
 Sof(H2B)=Sof(H13C)=Sof(H13D)=Sof(H14D)=Sof(H14E)=Sof(H14F)=Sof(C3A)=Sof(H3AA)=
 Sof(H3AB)=Sof(H3AC)=Sof(C1A)=Sof(H1AA)=Sof(H1AB)=Sof(H1AC)=Sof(C11A)=Sof(H11C)=
 Sof(H11D)=Sof(C12A)=Sof(H12A)=1-FVAR(1)
 Sof(C1)=Sof(H1A)=Sof(H1B)=Sof(H1C)=Sof(H2A)=Sof(C3)=Sof(H3A)=Sof(H3B)=
 Sof(H3C)=Sof(C11)=Sof(H11A)=Sof(H11B)=Sof(C12)=Sof(H12)=Sof(H13A)=Sof(H13B)=
 Sof(H14A)=Sof(H14B)=Sof(H14C)=FVAR(1)
6.a Ternary CH refined with riding coordinates:
 C2(H2A), C2(H2B), C5(H5), C12(H12), C16(H16), C19(H19), C24(H24), C12A(H12A)
6.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C13(H13A,H13B), C13(H13C,H13D), C23(H23A,H23B), C25(H25A,
 H25B), C11A(H11C,H11D)
6.c Aromatic/amide H refined with riding coordinates:
 N1(H1), N3(H3)
6.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C3(H3A,H3B,H3C), C6(H6A,H6B,H6C), C7(H7A,H7B,H7C), C14(H14A,
 H14B,H14C), C14(H14D,H14E,H14F), C15(H15A,H15B,H15C), C17(H17A,H17B,H17C),
 C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C28(H28A,H28B,H28C), C3A(H3AA,H3AB,
 H3AC), C1A(H1AA,H1AB,H1AC)
;
_shelx_res_checksum              45233
_shelx_hkl_checksum              28242
_olex2_submission_special_instructions 'No special instructions were received'