Pyramidalization/twisting of the amide functional group via remote steric congestion triggered by metal coordination.
Adachi, Shinya; Kumagai, Naoya; Shibasaki, Masakatsu; Chemical science 8 (2017) 85–90; doi:10.1039/c6sc03669d

data_1544201
_publ_section_title
;
 Pyramidalization/twisting of the amide functional group via remote steric
 congestion triggered by metal coordination.
;
_journal_issue                   1
_journal_name_full               'Chemical science'
_journal_page_first              85
_journal_page_last               90
_journal_paper_doi               10.1039/c6sc03669d
_journal_volume                  8
_journal_year                    2017
_chemical_formula_moiety         'C27 H20 F N3 O'
_chemical_formula_sum            'C27 H20 F N3 O'
_chemical_formula_weight         842.95
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2016-07-20 deposited with the CCDC.
2016-09-23 downloaded from the CCDC.
;
_cell_angle_alpha                90.050(2)
_cell_angle_beta                 96.320(2)
_cell_angle_gamma                117.495(3)
_cell_formula_units_Z            4
_cell_length_a                   12.2208(5)
_cell_length_b                   12.9781(4)
_cell_length_c                   15.6515(3)
_cell_measurement_reflns_used    12563
_cell_measurement_temperature    93
_cell_measurement_theta_max      73.42
_cell_measurement_theta_min      4.64
_cell_volume                     2184.84(13)
_computing_cell_refinement       'CrysAlisPro 1.171.39.4e (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.4e (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.4e (Rigaku OD, 2015)'
_computing_molecular_graphics    'CrystalStructure 4.2.1'
_computing_publication_material  'CrystalStructure 4.2.1 (Rigaku, 2015)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT Version 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      93
_diffrn_detector_area_resol_mean 5.811
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0825
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            15380
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.687
_diffrn_reflns_theta_max         73.710
_diffrn_reflns_theta_min         4.651
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.689
_exptl_absorpt_correction_T_max  0.955
_exptl_absorpt_correction_T_min  0.890
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.4e (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             880.00
_exptl_crystal_size_max          0.259
_exptl_crystal_size_mid          0.117
_exptl_crystal_size_min          0.067
_refine_diff_density_max         0.21
_refine_diff_density_min         -0.22
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     578
_refine_ls_number_reflns         15380
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0398
_refine_ls_R_factor_gt           0.0358
_refine_ls_shift/su_max          0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0637P)^2^+0.1383P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0996
_refine_ls_wR_factor_ref         0.1020
_reflns_Friedel_coverage         0.000
_reflns_number_gt                13604
_reflns_number_total             15380
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            c6sc03669d2.cif
_cod_data_source_block           xcalibur
_cod_depositor_comments
;

 Adding full bibliography for 1544197--1544204.cif.

2019-01-18
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_moiety     'C54 H40 F2 N6 O2'
_cod_original_formula_sum        'C54 H40 F2 N6 O2'
_cod_original_formula_units_Z    2
_cod_original_formula_weight     842.95
_cod_database_code               1544201
_shelx_res_checksum              81741