One-pot sequential synthesis of unsymmetrical diarylmethanes using methylene chloride as a C1-synthon.
Cui, Xueli; Chen, Chunming; Xie, Mei; Zhao, Taotao; Yi, Jianfeng; Sun, Weiqiang; Xiong, Zhuang; Hu, Jinhui; Wong, Wing-Leung; Wu, Jia-Qiang; Organic & biomolecular chemistry 22 (2024) 7965–7970; doi:10.1039/d4ob01158a

data_7160134
_publ_section_title
;
 One-pot sequential synthesis of unsymmetrical diarylmethanes using
 methylene chloride as a C1-synthon.
;
_journal_issue                   39
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              7965
_journal_page_last               7970
_journal_paper_doi               10.1039/d4ob01158a
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C17 H13 N3 O2'
_chemical_formula_sum            'C17 H13 N3 O2'
_chemical_formula_weight         291.30
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-04-24
_audit_creation_method
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_audit_update_record
;
2023-04-24 deposited with the CCDC.	2024-09-06 downloaded from the CCDC.
;
_cell_angle_alpha                97.6340(10)
_cell_angle_beta                 105.415(2)
_cell_angle_gamma                100.459(2)
_cell_formula_units_Z            4
_cell_length_a                   9.2049(2)
_cell_length_b                   12.7933(2)
_cell_length_c                   13.0136(2)
_cell_measurement_reflns_used    9856
_cell_measurement_temperature    297.0(2)
_cell_measurement_theta_max      76.6730
_cell_measurement_theta_min      3.5750
_cell_volume                     1426.06(5)
_computing_cell_refinement       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      297.0(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.952
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -61.00  22.00   0.50    1.00    --  -48.55  84.00  60.00  166
  2  \w    -17.00  75.00   0.50    1.00    --   48.55 -84.00 -59.00  184
  3  \w    -57.00 -24.00   0.50    3.00    --  -91.75  84.00  60.00   66
  4  \w   -108.00 -82.00   0.50    3.00    --  -91.75  84.00  60.00   52
  5  \w   -126.00 -80.00   0.50    3.00    --  -91.75 -84.00 -59.00   92
  6  \w    147.00 173.00   0.50    3.00    --  108.86  84.00  60.00   52
  7  \w   -120.00 -74.00   0.50    1.00    --  -48.55-125.00  90.00   92
  8  \w    -34.00  21.00   0.50    1.00    --  -48.55  38.00 -30.00  110
  9  \w   -114.00 -88.00   0.50    1.00    --  -48.55-125.00-180.00   52
 10  \w   -105.00 -77.00   0.50    1.00    --  -48.55-125.00-120.00   56
 11  \w   -107.00 -73.00   0.50    1.00    --  -48.55-125.00  60.00   68
 12  \w   -105.00 -79.00   0.50    1.00    --  -48.55-125.00  30.00   52
 13  \w    -11.00  18.00   0.50    1.00    --   48.55 -19.00 -60.00   58
 14  \w    -21.00   4.00   0.50    1.00    --   48.55 -19.00  30.00   50
 15  \w   -156.00 -95.00   0.50    3.00    --  -91.75 -99.00  60.00  122
 16  \w   -163.00-100.00   0.50    3.00    --  -91.75 -99.00-180.00  126
 17  \w   -122.00 -87.00   0.50    3.00    --  -91.75 -38.00  90.00   70
 18  \w   -159.00-103.00   0.50    3.00    --  -91.75 -99.00  30.00  112
 19  \w   -146.00 -92.00   0.50    3.00    --  -91.75 -99.00 -90.00  108
 20  \w   -165.00-133.00   0.50    3.00    --  -91.75 -38.00  90.00   64
 21  \w     41.00  66.00   0.50    3.00    --  108.86 -57.00 150.00   50
 22  \w     54.00 112.00   0.50    3.00    --  108.86-125.00 120.00  116
 23  \w     72.00  98.00   0.50    3.00    --  108.86 -99.00 120.00   52
 24  \w     95.00 130.00   0.50    3.00    --  108.86 125.00 -30.00   70
 25  \w     38.00  65.00   0.50    3.00    --  108.86 -57.00-180.00   54
 26  \w     36.00  61.00   0.50    3.00    --  108.86 -99.00 120.00   50
 27  \w     39.00  64.00   0.50    3.00    --  108.86 -57.00  90.00   50
 28  \w    127.00 157.00   0.50    3.00    --  108.86  38.00 -30.00   60
 29  \w     39.00 104.00   0.50    3.00    --  108.86-125.00  60.00  130
 30  \w     39.00 105.00   0.50    3.00    --  108.86-125.00  90.00  132
 31  \w     64.00 112.00   0.50    3.00    --  108.86-125.00 -90.00   96
 32  \w    140.00 178.00   0.50    3.00    --  108.86 125.00 -30.00   76
 33  \w     40.00  71.00   0.50    3.00    --  108.86-125.00-180.00   62
 34  \w     85.00 111.00   0.50    3.00    --  108.86-125.00-180.00   52
 35  \w     37.00  63.00   0.50    3.00    --  108.86 -57.00-150.00   52
 36  \w     42.00 105.00   0.50    3.00    --  108.86 -99.00-180.00  126
 37  \w    126.00 152.00   0.50    3.00    --  108.86  38.00 -60.00   52
 38  \w    103.00 177.00   0.50    3.00    --  108.86  19.00  90.00  148
 39  \w     50.00 104.00   0.50    3.00    --  108.86 -99.00 -60.00  108
 40  \w     38.00  63.00   0.50    3.00    --  108.86 -57.00 -30.00   50
 41  \w     39.00 106.00   0.50    3.00    --  108.86 -99.00 -90.00  134
 42  \w     37.00  66.00   0.50    3.00    --  108.86 -57.00 -60.00   58
 43  \w     77.00 102.00   0.50    3.00    --  108.86 -77.00  60.00   50
 44  \w     56.00  82.00   0.50    3.00    --  108.86 -84.00 -59.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0420991000
_diffrn_orient_matrix_UB_12      0.1101044000
_diffrn_orient_matrix_UB_13      0.0777782000
_diffrn_orient_matrix_UB_21      -0.1729811000
_diffrn_orient_matrix_UB_22      0.0006810000
_diffrn_orient_matrix_UB_23      -0.0243700000
_diffrn_orient_matrix_UB_31      -0.0090242000
_diffrn_orient_matrix_UB_32      -0.0586455000
_diffrn_orient_matrix_UB_33      0.0949068000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0208
_diffrn_reflns_av_unetI/netI     0.0215
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.952
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            18082
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.952
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.623
_diffrn_reflns_theta_min         3.579
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.747
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61045
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.122a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_description       block
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.434
_refine_diff_density_min         -0.439
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     349
_refine_ls_number_reflns         5797
_refine_ls_number_restraints     74
_refine_ls_restrained_S_all      1.121
_refine_ls_R_factor_all          0.0706
_refine_ls_R_factor_gt           0.0623
_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^)+(0.0830P)^2^+0.4697P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1773
_refine_ls_wR_factor_ref         0.1847
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4842
_reflns_number_total             5797
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob01158a2.cif
_cod_data_source_block           exp_5558_auto
_cod_depositor_comments          'Adding full bibliography for 7160134.cif.'
_cod_database_code               7160134
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.865
_shelx_estimated_absorpt_t_min   0.807
_reflns_odcompleteness_completeness 99.78
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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. Restrained distances
 O1-N1 \\sim O2-N1
 with sigma of 0.02
 O3-N4 \\sim O4-N4
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
O1 \\sim O2: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02
within 2A
Uanis(C13) \\sim Ueq, Uanis(C14) \\sim Ueq, Uanis(C15) \\sim Ueq, Uanis(C16)
\\sim Ueq, Uanis(C17) \\sim Ueq, Uanis(C12) \\sim Ueq: with sigma of 0.01 and
sigma for terminal atoms of 0.02
Uanis(C29) \\sim Ueq, Uanis(C30) \\sim Ueq, Uanis(C31) \\sim Ueq, Uanis(C32)
\\sim Ueq, Uanis(C33) \\sim Ueq, Uanis(C34) \\sim Ueq: with sigma of 0.01 and
sigma for terminal atoms of 0.02
Uanis(C16) \\sim Ueq, Uanis(C15) \\sim Ueq, Uanis(C14) \\sim Ueq, Uanis(C13)
\\sim Ueq, Uanis(C12) \\sim Ueq, Uanis(C17) \\sim Ueq: with sigma of 0.03 and
sigma for terminal atoms of 0.06
Uanis(C33) \\sim Ueq, Uanis(C32) \\sim Ueq, Uanis(C31) \\sim Ueq, Uanis(C30)
\\sim Ueq, Uanis(C29) \\sim Ueq, Uanis(C34) \\sim Ueq: with sigma of 0.03 and
sigma for terminal atoms of 0.06
4.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C26(H26A,H26B)
4.b Aromatic/amide H refined with riding coordinates:
 N2(H2), N6(H6), N5(H5), N3(H3), C4(H4), C3(H3A), C2(H2A), C15(H15), C14(H14),
 C17(H17), C16(H16), C20(H20), C21(H21), C19(H19), C34(H34), C33(H33), C32(H32),
  C31(H31), C8(H8), C28(H28), C25(H25), C11(H11)
4.c Fitted hexagon refined as free rotating group:
 C4(C3,C1,C2,C5,C6), C15(C14,C13,C12,C17,C16), C18(C20,C21,C23,C22,C19),
 C30(C29,C34,C33,C32,C31)
;
_shelx_res_checksum              39069
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.633
_oxdiff_exptl_absorpt_empirical_full_min 0.811