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_7241270
_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         'C17 H16 N2 O2'
_chemical_formula_sum            'C17 H16 N2 O2'
_chemical_formula_weight         280.32
_chemical_melting_point          373-340
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2019-09-26
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-07-28 deposited with the CCDC.	2020-09-17 downloaded from the CCDC.
;
_cell_angle_alpha                102.971(7)
_cell_angle_beta                 101.832(7)
_cell_angle_gamma                113.041(8)
_cell_formula_units_Z            2
_cell_length_a                   8.6964(8)
_cell_length_b                   9.2214(7)
_cell_length_c                   10.4886(8)
_cell_measurement_reflns_used    2531
_cell_measurement_temperature    150.01(10)
_cell_measurement_theta_max      30.3790
_cell_measurement_theta_min      2.5540
_cell_volume                     712.90(13)
_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 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    2.50    --  -19.89 -62.00  38.11   86
  2  \w    -86.00   0.00   1.00    2.50    --  -19.89 -64.00-134.56   86
  3  \w      3.00  84.00   1.00    2.50    --   20.05  57.00   0.00   81
  4  \w     10.00  56.00   1.00    2.50    --   20.05  57.00-180.00   46
  5  \w      1.00  53.00   1.00    2.50    --   20.05  65.00 -94.72   52
  6  \w    -44.00  17.00   1.00    2.50    --   20.05 -57.00-180.00   61
  7  \w    -41.00   9.00   1.00    2.50    --   20.05 -19.00-120.00   50
  8  \w      0.00  87.00   1.00    2.50    --   20.05  65.00  76.57   87
;
_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      -0.0419341000
_diffrn_orient_matrix_UB_12      -0.0679048000
_diffrn_orient_matrix_UB_13      -0.0635006000
_diffrn_orient_matrix_UB_21      -0.0467113000
_diffrn_orient_matrix_UB_22      0.0401171000
_diffrn_orient_matrix_UB_23      -0.0275926000
_diffrn_orient_matrix_UB_31      0.0696690000
_diffrn_orient_matrix_UB_32      0.0408587000
_diffrn_orient_matrix_UB_33      -0.0244404000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0298
_diffrn_reflns_av_unetI/netI     0.0429
_diffrn_reflns_Laue_measured_fraction_full 0.999
_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       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            8910
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.274
_diffrn_reflns_theta_min         2.551
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.757
_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    1.306
_exptl_crystal_description       block
_exptl_crystal_F_000             296
_exptl_crystal_recrystallization_method
'Slow evaporation from a diethyl ether solution.'
_exptl_crystal_size_max          0.475
_exptl_crystal_size_mid          0.406
_exptl_crystal_size_min          0.286
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         3523
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0656
_refine_ls_R_factor_gt           0.0472
_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^)+(0.0428P)^2^+0.1525P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1024
_refine_ls_wR_factor_ref         0.1135
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2719
_reflns_number_total             3523
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ce01137a2.cif
_cod_data_source_block           jb423absbeam
_cod_original_cell_volume        712.90(11)
_cod_database_code               7241270
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C17 H16 O2 N2'
_chemical_oxdiff_usercomment     'Yellow Block'
_reflns_odcompleteness_completeness 99.80
_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), C4(H4), C6(H6), C7(H7), C8(H8), C13(H13)
2.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C17(H17A,H17B,H17C)
;
_shelx_res_checksum              13594
_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 1.061
_oxdiff_exptl_absorpt_empirical_full_min 0.934