Brønsted Acid-Catalyzed Cyanotritylation of Aldehydes by Trityl Isocyanide.
Cioc, Răzvan C; Schuckman, Peter; Preschel, Hans D.; Vlaar, Tjøstil; Ruijter, Eelco; Orru, Romano V. A.; Organic letters 18 (2016) 3562–3565; doi:10.1021/acs.orglett.6b01481

data_1555594
_publ_section_title
;
 Br\/onsted Acid-Catalyzed Cyanotritylation of Aldehydes by Trityl
 Isocyanide.
;
_journal_issue                   15
_journal_name_full               'Organic letters'
_journal_page_first              3562
_journal_page_last               3565
_journal_paper_doi               10.1021/acs.orglett.6b01481
_journal_volume                  18
_journal_year                    2016
_chemical_absolute_configuration S
_chemical_formula_moiety         'C27 H21 N1 O1'
_chemical_formula_sum            'C27 H21 N O'
_chemical_formula_weight         375.45
_chemical_melting_point          390.0(10)
_chemical_name_common            3m
_chemical_name_systematic        (S)-2-phenyl-2-(trityloxy)acetonitrile
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     vecmap
_atom_sites_solution_secondary   vecmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 95.0970(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.76560(10)
_cell_length_b                   8.67320(10)
_cell_length_c                   11.05480(10)
_cell_measurement_reflns_used    55026
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      75.1390
_cell_measurement_theta_min      3.9460
_cell_volume                     1028.129(18)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Mercury 3.5'
_computing_publication_material  PLATON
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXD (Sheldrick, 2014)'
_diffrn_ambient_temperature      100.0(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4839
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_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  0.0880
_diffrn_reflns_av_unetI/netI     0.0208
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            116535
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.573
_diffrn_reflns_theta_min         4.015
_diffrn_source                   'sealed tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.568
_exptl_absorpt_correction_T_max  0.969
_exptl_absorpt_correction_T_min  0.914
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.213
_exptl_crystal_density_meas      ?
_exptl_crystal_description       block
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.3296
_exptl_crystal_size_mid          0.1349
_exptl_crystal_size_min          0.1017
_refine_diff_density_max         0.175
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details
;
 Flack x determined using 1811 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(12)
_refine_ls_extinction_coef       0.0076(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         4247
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0453
_refine_ls_R_factor_gt           0.0430
_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^)+(0.0751P)^2^+0.1803P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1106
_refine_ls_wR_factor_ref         0.1134
_reflns_Friedel_coverage         0.867
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.992
_reflns_number_gt                4059
_reflns_number_total             4247
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b01481_si_002.cif
_cod_data_source_block           3m
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '389-391K' was changed to
'390.0(10)' -- the average value was taken and precision was
estimated.

data item '_exptl_crystal_density_meas' value 'not measured' was
changed to '?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1555594
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              15914
_shelx_hkl_checksum              87440