Squaramide-catalysed asymmetric Friedel-Crafts alkylation of naphthol and unsaturated pyrazolones.
Wei, Ran; Gao, Li; Li, Gaihui; Tang, Li; Zhang, Guoshun; Zheng, Feilang; Song, Heng; Li, Qingshan; Ban, Shurong; Organic & biomolecular chemistry 19 (2021) 3370–3373; doi:10.1039/d1ob00347j

data_7157973
_publ_section_title
;
 Squaramide-catalysed asymmetric Friedel-Crafts alkylation of naphthol and
 unsaturated pyrazolones.
;
_journal_issue                   15
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3370
_journal_page_last               3373
_journal_paper_doi               10.1039/d1ob00347j
_journal_volume                  19
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C27 H22 N2 O2, 0.5(C H2 Cl2)'
_chemical_formula_sum            'C27.5 H23 Cl N2 O2'
_chemical_formula_weight         448.93
_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
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2021-01-05 deposited with the CCDC.	2021-03-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.396(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.2574(2)
_cell_length_b                   8.05500(10)
_cell_length_c                   18.4264(4)
_cell_measurement_reflns_used    8936
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      75.962
_cell_measurement_theta_min      2.413
_cell_volume                     2250.48(6)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       \w\k
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0535
_diffrn_reflns_av_unetI/netI     0.0442
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            24009
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.952
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         75.962
_diffrn_reflns_theta_min         2.413
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    1.721
_exptl_absorpt_correction_T_max  0.998
_exptl_absorpt_correction_T_min  0.996
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ' Higashi, T. (1995)'
_exptl_crystal_colour            ??colourless??
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_description       needle
_exptl_crystal_F_000             940
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.731
_refine_diff_density_min         -0.336
_refine_diff_density_rms         0.074
_refine_ls_abs_structure_details
;
 Flack x determined using 2931 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.037(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     586
_refine_ls_number_reflns         8936
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.0711
_refine_ls_R_factor_gt           0.0613
_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^)+(0.1137P)^2^+0.1530P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1605
_refine_ls_wR_factor_ref         0.1680
_reflns_Friedel_coverage         0.813
_reflns_Friedel_fraction_full    0.975
_reflns_Friedel_fraction_max     0.922
_reflns_number_gt                7555
_reflns_number_total             8936
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob00347j2.cif
_cod_data_source_block           BSR-1-100K
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 7157973.cif.

2024-11-08
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_sg_symbol_H-M      'P 21'
_cod_original_formula_moiety     '2(C27 H22 N2 O2), C H2 Cl2'
_cod_original_formula_sum        'C55 H46 Cl2 N4 O4'
_cod_original_formula_units_Z    2
_cod_original_formula_weight     897.86
_cod_database_code               7157973
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              9929