Selective synthesis of mono- and di-methylated amines using methanol and sodium azide as C1 and N1 sources
Chakrabarti, Kaushik; Mishra, Anju; Panja, Dibyajyoti; Paul, Bhaskar; Kundu, Sabuj; Green Chemistry 20 (2018) 3339–; doi:10.1039/C8GC00863A

data_7230906
_publ_section_title
;
 Selective synthesis of mono- and di-methylated amines using methanol and
 sodium azide as C1 and N1 sources
;
_journal_issue                   14
_journal_name_full               'Green Chemistry'
_journal_page_first              3339
_journal_paper_doi               10.1039/C8GC00863A
_journal_volume                  20
_journal_year                    2018
_chemical_formula_moiety         'C53 H44 Cl N4 P2 Ru, F6 P'
_chemical_formula_sum            'C53 H44 Cl F6 N4 P3 Ru'
_chemical_formula_weight         1080.35
_space_group_crystal_system      tetragonal
_space_group_IT_number           82
_space_group_name_Hall           'I -4'
_space_group_name_H-M_alt        'I -4'
_symmetry_space_group_name_Hall  'I -4'
_symmetry_space_group_name_H-M   'I -4'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2017-11-02
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2017-11-06 deposited with the CCDC.
2018-06-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   28.6436(9)
_cell_length_b                   28.6436(9)
_cell_length_c                   13.5364(5)
_cell_measurement_reflns_used    9968
_cell_measurement_temperature    100
_cell_measurement_theta_max      21.73
_cell_measurement_theta_min      2.19
_cell_volume                     11106.0(6)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1231
_diffrn_reflns_av_unetI/netI     0.0864
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            68029
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.047
_diffrn_reflns_theta_max         25.047
_diffrn_reflns_theta_min         2.011
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.473
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6252
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.0749 before and 0.0639 after correction.
The Ratio of minimum to maximum transmission is 0.8384.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            orangish
_exptl_crystal_colour_modifier   orangish
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_description       needle
_exptl_crystal_F_000             4400
_exptl_crystal_size_max          0.01
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_refine_diff_density_max         1.404
_refine_diff_density_min         -0.757
_refine_diff_density_rms         0.210
_refine_ls_abs_structure_details
;
 Flack x determined using 2855 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.013(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.119
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     615
_refine_ls_number_reflns         9816
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.119
_refine_ls_R_factor_all          0.1039
_refine_ls_R_factor_gt           0.0714
_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/[\s^2^(Fo^2^)+(0.1362P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1913
_refine_ls_wR_factor_ref         0.2157
_reflns_Friedel_coverage         0.910
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                7479
_reflns_number_total             9816
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8gc00863a2.cif
_cod_data_source_block           KC_Com_E
_cod_depositor_comments          'Adding full bibliography for 7230906.cif.'
_cod_original_cell_volume        11106.0(8)
_cod_database_code               7230906
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.995
_shelx_estimated_absorpt_t_min   0.995
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C34(H34), C24(H24), C16(H16), C50(H50), C49(H49), C44(H44), C14(H14),
 C48(H48), C3(H3), C13(H13), C20(H20), C11(H11), C25(H25), C1(H1), C00S(H00S),
 C29(H29), C12(H12), C46(H46), C43(H43), C26(H26), C014(H014), C5(H5),
 C018(H018), C22(H22), C21(H21), C28(H28), C27(H27), C4(H4), C45(H45), C17(H17),
  C32(H32), C38(H38), C36(H36), C18(H18), C30(H30), C37(H37), C31(H31), C51(H51)
2.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C9(H9A,H9B,H9C)
;
_shelx_res_checksum              82546
_shelx_fab_checksum              65614
_olex2_submission_special_instructions 'No special instructions were received'