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_7241269
_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         'C18 H18 N4'
_chemical_formula_sum            'C18 H18 N4'
_chemical_formula_weight         290.36
_chemical_melting_point          379.5(15)
_chemical_name_systematic
2-Cyano-3-(4?-,8?-bis(dimethylamino)naphthalen-1?-yl)propenenitrile
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2019-04-08
_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                 114.584(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   20.7770(7)
_cell_length_b                   9.3348(2)
_cell_length_c                   18.1408(6)
_cell_measurement_reflns_used    6879
_cell_measurement_temperature    150.01(10)
_cell_measurement_theta_max      30.5490
_cell_measurement_theta_min      2.4560
_cell_volume                     3199.46(19)
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9832
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 1.000
_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    -37.00  47.00   0.75    7.50    --  -19.97  57.00  30.00  112
  2  \w      1.00  88.00   0.75    7.50    --   20.20  37.00-180.00  116
  3  \w    -49.00  38.00   0.75    7.50    --   20.20 -37.00-180.00  116
  4  \w      7.00  88.00   0.75    7.50    --   20.20  37.00 -30.00  108
;
_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      -0.0096835000
_diffrn_orient_matrix_UB_12      -0.0313755000
_diffrn_orient_matrix_UB_13      0.0295121000
_diffrn_orient_matrix_UB_21      -0.0157828000
_diffrn_orient_matrix_UB_22      -0.0582067000
_diffrn_orient_matrix_UB_23      -0.0265339000
_diffrn_orient_matrix_UB_31      0.0326654000
_diffrn_orient_matrix_UB_32      -0.0374937000
_diffrn_orient_matrix_UB_33      0.0165285000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0318
_diffrn_reflns_av_unetI/netI     0.0412
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            24059
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.282
_diffrn_reflns_theta_min         2.434
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.882
_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            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.206
_exptl_crystal_description       block
_exptl_crystal_F_000             1232
_exptl_crystal_recrystallization_method
'Slow evaporation from a dichloromethane solution'
_exptl_crystal_size_max          0.543
_exptl_crystal_size_mid          0.415
_exptl_crystal_size_min          0.304
_refine_diff_density_max         0.226
_refine_diff_density_min         -0.329
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     405
_refine_ls_number_reflns         7948
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0843
_refine_ls_R_factor_gt           0.0637
_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^)+(0.0456P)^2^+1.3704P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1268
_refine_ls_wR_factor_ref         0.1364
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6245
_reflns_number_total             7948
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ce01137a2.cif
_cod_data_source_block           in063absbeam
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '378-381' was changed to
'379.5(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_database_code               7241269
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C18 N4 H18'
_chemical_oxdiff_usercomment     'Orange Block '
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.22
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C33(H33), C4(H4), C26(H26), C15(H15), C22(H22), C25(H25), C7(H7), C8(H8),
 C20(H20), C3(H3), C21(H21), C2(H2)
2.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C29(H29A,H29B,H29C), C31(H31A,H31B,
 H31C), C32(H32A,H32B,H32C), C30(H30A,H30B,H30C), C11(H11A,H11B,H11C), C12(H12A,
 H12B,H12C)
;
_shelx_res_checksum              18265
_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 1.045
_oxdiff_exptl_absorpt_empirical_full_min 0.972