Four related diethyl [(arylamino)(4-ethynylphenyl)methyl]phosphonates
Ouahrouch, Abdelaaziz; Krim, Jamal; Taourirte, Moha; Lazrek, Hassan B.; Engels, Joachim W.; Bats, Jan W.; Acta Crystallographica Section C 69 (2013) 1157–1163; doi:10.1107/S0108270113022981

data_2019170
_publ_section_title
;
 Four related diethyl [(arylamino)(4-ethynylphenyl)methyl]phosphonates
;
_journal_coeditor_code           FG3306
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1157
_journal_page_last               1163
_journal_paper_doi               10.1107/S0108270113022981
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C19 H21 Br N O3 P'
_chemical_formula_moiety         'C19 H21 Br N O3 P'
_chemical_formula_sum            'C19 H21 Br N O3 P'
_chemical_formula_weight         422.25
_chemical_melting_point          416.0(10)
_chemical_name_systematic
;
Diethyl [(4-bromoanilino)(4-ethynylphenyl)methyl]phosphonate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 104.1140(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.9339(7)
_cell_length_b                   16.5179(11)
_cell_length_c                   11.1325(7)
_cell_measurement_reflns_used    7719
_cell_measurement_temperature    186(2)
_cell_measurement_theta_max      27
_cell_measurement_theta_min      3
_cell_volume                     1949.9(2)
_computing_cell_refinement       'SAINT (Siemens, 1995)'
_computing_data_collection       'SMART (Siemens, 1995)'
_computing_data_reduction        'SAINT (Siemens, 1995)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      186(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Siemens SMART 1K CCD area-detector'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_av_sigmaI/netI    0.0295
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            22735
_diffrn_reflns_theta_full        28.20
_diffrn_reflns_theta_max         28.20
_diffrn_reflns_theta_min         2.25
_diffrn_standards_decay_%        0.0
_diffrn_standards_interval_time  900
_diffrn_standards_number         564
_exptl_absorpt_coefficient_mu    2.207
_exptl_absorpt_correction_T_max  0.332
_exptl_absorpt_correction_T_min  0.284
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2000)'
_exptl_crystal_colour            pale_brown
_exptl_crystal_density_diffrn    1.438
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.60
_exptl_crystal_size_min          0.50
_refine_diff_density_max         0.465
_refine_diff_density_min         -0.432
_refine_ls_extinction_coef       0.0039(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         4762
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.0478
_refine_ls_R_factor_gt           0.0376
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.025P)^2^+1.3P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0750
_refine_ls_wR_factor_ref         0.0787
_reflns_number_gt                4104
_reflns_number_total             4762
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            fg3306.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2019170