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_7241265
_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         'C28 H21 N3, C7 H8'
_chemical_formula_sum            'C35 H29 N3'
_chemical_formula_weight         491.61
_chemical_melting_point          412.0(10)
_chemical_name_systematic
2-Cyano-3-((8?-(dimethylamino)-4?,5?-diphenylnaphthalen-1?-yl)propenenitrile
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2019-09-24
_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                81.716(3)
_cell_angle_beta                 77.638(3)
_cell_angle_gamma                78.624(3)
_cell_formula_units_Z            2
_cell_length_a                   8.6923(3)
_cell_length_b                   12.6464(5)
_cell_length_c                   12.8192(5)
_cell_measurement_reflns_used    10710
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      29.9340
_cell_measurement_theta_min      3.4900
_cell_volume                     1341.80(9)
_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 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(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 0.998
_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    -87.00  -1.00   1.00   45.00    --  -19.81 -63.00 -54.64   86
  2  \w    -86.00   0.00   1.00   45.00    --  -19.81 -65.00-114.15   86
  3  \w    -87.00  -3.00   1.00   45.00    --  -19.81 -57.00  60.00   84
  4  \w    -87.00  -2.00   1.00   45.00    --  -19.81 -60.00  25.62   85
  5  \w    -47.00  40.00   1.00   45.00    --   19.89 -65.00-179.83   87
  6  \w      0.00  86.00   1.00   45.00    --   19.89  65.00-147.97   86
  7  \f    126.00 180.00   1.00   45.00  40.00  19.89   0.00    --    54
  8  \w      0.00  86.00   1.00   45.00    --   19.89  64.00 -33.97   86
  9  \w      0.00  86.00   1.00   45.00    --   19.89  65.00-119.27   86
 10  \w    -37.00  47.00   1.00   45.00    --  -19.81  57.00   0.00   84
 11  \w    -47.00  37.00   1.00   45.00    --   19.89 -57.00 -90.00   84
 12  \w      3.00  87.00   1.00   45.00    --   19.89  57.00 150.00   84
 13  \w    -47.00  40.00   1.00   45.00    --   19.89 -65.00  -1.56   87
 14  \w    -47.00  40.00   1.00   45.00    --   19.89 -65.00-133.82   87
 15  \w    -47.00  37.00   1.00   45.00    --   19.89 -57.00 120.00   84
 16  \w    -47.00  39.00   1.00   45.00    --   19.89 -63.00  78.38   86
 17  \w    -47.00  37.00   1.00   45.00    --   19.89 -57.00 -60.00   84
 18  \w      3.00  87.00   1.00   45.00    --   19.89  57.00  30.00   84
 19  \w    -47.00 -22.00   1.00   45.00    --   19.89 -57.00  90.00   25
 20  \w    -47.00  38.00   1.00   45.00    --   19.89 -62.00  23.56   85
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0448668000
_diffrn_orient_matrix_UB_12      0.0512877000
_diffrn_orient_matrix_UB_13      0.0127822000
_diffrn_orient_matrix_UB_21      0.0202399000
_diffrn_orient_matrix_UB_22      0.0214176000
_diffrn_orient_matrix_UB_23      -0.0544401000
_diffrn_orient_matrix_UB_31      -0.0690585000
_diffrn_orient_matrix_UB_32      -0.0148803000
_diffrn_orient_matrix_UB_33      -0.0108719000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0572
_diffrn_reflns_av_unetI/netI     0.0467
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            43402
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.281
_diffrn_reflns_theta_min         3.170
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.921
_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_density_diffrn    1.217
_exptl_crystal_description       plate
_exptl_crystal_F_000             520
_exptl_crystal_recrystallization_method
'Slow evaporation from a toluene solution'
_exptl_crystal_size_max          0.303
_exptl_crystal_size_mid          0.115
_exptl_crystal_size_min          0.062
_refine_diff_density_max         0.348
_refine_diff_density_min         -0.343
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.153
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     346
_refine_ls_number_reflns         6656
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.153
_refine_ls_R_factor_all          0.0920
_refine_ls_R_factor_gt           0.0727
_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^)+(0.0350P)^2^+0.9907P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1296
_refine_ls_wR_factor_ref         0.1377
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5540
_reflns_number_total             6656
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ce01137a2.cif
_cod_data_source_block           jb_staceydintrile100kabs
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '411-413' was changed to
'412.0(10)' -- 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               7241265
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C35 H33 N3'
_chemical_oxdiff_usercomment     'Orange Plate'
_reflns_odcompleteness_completeness 99.79
_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:
 C2(H2), C3(H3), C7(H7), C8(H8), C14(H14), C15(H15), C16(H16), C17(H17),
 C18(H18), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25), C30(H30),
  C31(H31), C32(H32), C33(H33), C34(H34)
2.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C35(H35A,H35B,H35C)
;
_shelx_res_checksum              63822
_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 1.082
_oxdiff_exptl_absorpt_empirical_full_min 0.880