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_7241266
_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_moiety         'Cl, H O0.5, C18 H19 N4'
_chemical_formula_sum            'C18 H20 Cl N4 O0.5'
_chemical_formula_weight         335.83
_chemical_melting_point          441.5(15)
_chemical_name_systematic
'2-Cyano-3-(8?-dimethylamino-4?-dimethylammonio-naphthalen-1?-yl)propene-nitrile 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_date             2019-04-15
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_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                   44.6586(17)
_cell_length_b                   22.6565(7)
_cell_length_c                   6.8837(4)
_cell_measurement_reflns_used    4444
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      28.9700
_cell_measurement_theta_min      3.7240
_cell_volume                     6965.0(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_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9832
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -33.00  51.00   1.00   25.00    --  -16.16  57.00 -30.00   84
  2  \w    -83.00   1.00   1.00   25.00    --  -16.16 -57.00 150.00   84
  3  \w    -13.00  88.00   1.00   25.00    --   16.24  19.00 -90.00  101
  4  \w    -33.00  -8.00   1.00   25.00    --  -16.16  57.00-180.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0124886000
_diffrn_orient_matrix_UB_12      0.0180821000
_diffrn_orient_matrix_UB_13      -0.0224389000
_diffrn_orient_matrix_UB_21      0.0074585000
_diffrn_orient_matrix_UB_22      -0.0104126000
_diffrn_orient_matrix_UB_23      0.0843094000
_diffrn_orient_matrix_UB_31      0.0063541000
_diffrn_orient_matrix_UB_32      -0.0233229000
_diffrn_orient_matrix_UB_33      -0.0550078000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0275
_diffrn_reflns_av_unetI/netI     0.0362
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       59
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            11058
_diffrn_reflns_point_group_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.913
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.272
_diffrn_reflns_theta_min         3.275
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.228
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.840
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
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            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_description       needle
_exptl_crystal_F_000             2832
_exptl_crystal_recrystallization_method
'Slow evaporation from a methanol solution.'
_exptl_crystal_size_max          0.441
_exptl_crystal_size_mid          0.142
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details
;
 Flack x determined using 1448 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     225
_refine_ls_number_reflns         3948
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.097
_refine_ls_R_factor_all          0.0389
_refine_ls_R_factor_gt           0.0357
_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^)+(0.0355P)^2^+3.8840P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0751
_refine_ls_wR_factor_ref         0.0764
_reflns_Friedel_coverage         0.738
_reflns_Friedel_fraction_full    0.942
_reflns_Friedel_fraction_max     0.845
_reflns_number_gt                3763
_reflns_number_total             3948
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ce01137a2.cif
_cod_data_source_block           in063abs100k
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '440-443' was changed to
'441.5(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_cell_volume        6964.9(5)
_cod_original_formula_sum        'C18 H20 Cl N4 O0.50'
_cod_database_code               7241266
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C18 H18 N4 Cl1'
_shelx_estimated_absorpt_t_max   0.971
_shelx_estimated_absorpt_t_min   0.906
_reflns_odcompleteness_completeness 99.65
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 N2(H2)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2A), C3(H3), C4(H4), C7(H7), C8(H8)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C14(H14A,H14B,
 H14C)
;
_shelx_res_checksum              18294
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.072
_oxdiff_exptl_absorpt_empirical_full_min 0.917