Modelling of an Aza-Michael Reaction from Crystalline Naphthalene Derivatives Containing Peri-Peri Interactions: Very Long N-C Bonds?
Bristow, Jonathan; Naftalin, Isaac; Cliff, Stacey V. A.; Yang, Songjie; Wallis, John D.; Carravetta, Marina; Heinmaa, Ivo; Stern, Raivo; CrystEngComm  (2020) –; doi:10.1039/D0CE01137A

data_7241267
_publ_section_title
;
 Modelling of an Aza-Michael Reaction from Crystalline Naphthalene
 Derivatives Containing Peri-Peri Interactions: Very&#x00A0;Long N-C
 Bonds?
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D0CE01137A
_journal_year                    2020
_chemical_formula_sum            'C19 H23 Cl N3 O2.5'
_chemical_formula_weight         368.85
_chemical_melting_point          398.5(15)
_chemical_name_systematic
'Methyl E-2-cyano-3-(8?-dimethylamino-4?-dimethylammonio-naphthalen-1?-yl)-2-propenoate chloride'
_space_group_crystal_system      orthorhombic
_space_group_IT_number           43
_space_group_name_Hall           'F 2 -2d'
_space_group_name_H-M_alt        'F d d 2'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-2014
_audit_update_record
;
2020-07-16 deposited with the CCDC.	2020-09-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   48.4820(18)
_cell_length_b                   22.8029(9)
_cell_length_c                   6.7460(3)
_cell_measurement_reflns_used    3784
_cell_measurement_temperature    260(2)
_cell_measurement_theta_max      22.3370
_cell_measurement_theta_min      3.6700
_cell_volume                     7457.9(5)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    SHELXS-97
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      260.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9832
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0561
_diffrn_reflns_av_unetI/netI     0.0851
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       61
_diffrn_reflns_limit_h_min       -64
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            11484
_diffrn_reflns_point_group_measured_fraction_full 0.962
_diffrn_reflns_point_group_measured_fraction_max 0.928
_diffrn_reflns_theta_full        27.500
_diffrn_reflns_theta_max         28.261
_diffrn_reflns_theta_min         3.362
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.225
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97473
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_description       block
_exptl_crystal_F_000             3120
_exptl_crystal_recrystallization_method
'Slow evaporation from an acetonitrile solution'
_exptl_crystal_size_max          0.259
_exptl_crystal_size_mid          0.228
_exptl_crystal_size_min          0.083
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details
;
 Flack x determined using 954 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         4286
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0965
_refine_ls_R_factor_gt           0.0600
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0308P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0921
_refine_ls_wR_factor_ref         0.1070
_reflns_Friedel_coverage         0.775
_reflns_Friedel_fraction_full    0.934
_reflns_Friedel_fraction_max     0.885
_reflns_number_gt                2977
_reflns_number_total             4286
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ce01137a2.cif
_cod_data_source_block           400JW260
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '397-400' was changed to
'398.5(15)' -- the average value was taken and precision was
estimated.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_original_formula_sum        'C19 H23 Cl N3 O2.50'
_cod_database_code               7241267
_shelxl_version_number           2014-3
_shelx_res_checksum              96821