Conformational flexibility in amidophosphoesters: a CSD analysis completed with two new crystal structures of (C~6~H~5~O)~2~P(O)<i>X</i> [<i>X</i>~= NHC~7~H~13~ and N(CH~2~C~6~H~5~)~2~]
Vahdani Alviri, Banafsheh; Pourayoubi, Mehrdad; Abdul Salam, Abdul Ajees; Nečas, Marek; van der Lee, Arie; Chithran, Akshara; Damodaran, Krishnan; Acta Crystallographica Section C 76 (2020) 104–116; doi:10.1107/S2053229619016619

data_2021851
_publ_section_title
;
 Conformational flexibility in amidophosphoesters: a CSD analysis
 completed with two new crystal structures of (C~6~H~5~O)~2~P(O)<i>X</i>
 [<i>X</i>~= NHC~7~H~13~ and N(CH~2~C~6~H~5~)~2~]
;
_journal_coeditor_code           YO3071
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              104
_journal_page_last               116
_journal_paper_doi               10.1107/S2053229619016619
_journal_volume                  76
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_iupac          'C19 H24 N O3 P'
_chemical_formula_moiety         'C19 H24 N O3 P'
_chemical_formula_sum            'C19 H24 N O3 P'
_chemical_formula_weight         345.36
_chemical_name_systematic
;
Diphenyl (cycloheptylamido)phosphate
;
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     iterative
_audit_creation_method           CRYSTALS_ver_14.61
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.3538(2)
_cell_length_b                   9.7899(3)
_cell_length_c                   19.3432(5)
_cell_measurement_reflns_used    3874
_cell_measurement_temperature    175
_cell_measurement_theta_max      27.0750
_cell_measurement_theta_min      2.1150
_cell_volume                     1771.31(8)
_computing_cell_refinement
;
CrysAlis PRO (Rigaku OD, 2015)
;
_computing_data_collection
;
CrysAlis PRO (Rigaku OD, 2015)
;
_computing_data_reduction
;
CrysAlis PRO (Rigaku OD, 2015)
;
_computing_molecular_graphics
;
CAMERON (Watkin <i>et al.</i>, 1996) and
<i>PyMOL</i> (Schr\"odinger, 2015)
;
_computing_publication_material
;
CRYSTALS (Betteridge <i>et al.</i>,  2003)
;
_computing_structure_refinement
;
CRYSTALS (Betteridge <i>et al.</i>, 2003)
;
_computing_structure_solution
;
SUPERFLIP (Palatinus & Chapuis, 2007)
;
_diffrn_ambient_temperature      175
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0143
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.869
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Rigaku Xcalibur Sapphire3 Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.035
_diffrn_reflns_av_unetI/netI     0.0487
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            9026
_diffrn_reflns_theta_full        25.169
_diffrn_reflns_theta_max         27.965
_diffrn_reflns_theta_min         2.106
_exptl_absorpt_coefficient_mu    0.172
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97846
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Rigaku OD, 2015)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_description       prism
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.32
_refine_diff_density_min         -0.54
_refine_ls_abs_structure_details
;
Flack (1983), 1505 Friedel-pairs
;
_refine_ls_abs_structure_Flack   0.6(3)
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9502
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         3338
_refine_ls_number_restraints     79
_refine_ls_R_factor_all          0.0607
_refine_ls_R_factor_gt           0.0522
_refine_ls_shift/su_max          0.0004984
_refine_ls_shift/su_mean         0.0000848
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince,
1982)
[weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)]
where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax
Method = Robust Weighting (Prince, 1982)
W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^
A~i~ are:
19.6 25.7 7.98
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1054
_refine_ls_wR_factor_gt          0.0964
_refine_ls_wR_factor_ref         0.1028
_reflns_number_gt                2964
_reflns_number_total             3411
_reflns_threshold_expression     I>2.0\s(I)
_cod_data_source_file            yo3071sup1.cif
_cod_data_source_block           I
_cod_depositor_comments
'Adding full bibliography for 2021851--2021852.cif.'
_cod_original_cell_volume        1771.31(5)
_cod_original_sg_symbol_H-M      'P n a 21 '
_cod_database_code               2021851
_cod_database_fobs_code          2021851