Interaction, bond formation or reaction between a dimethylamino group and an adjacent alkene or aldehyde group in aromatic systems controlled by remote molecular constraints
Bristow, Jonathan C.; Cliff, Stacey V. A.; Yang, Songjie; Wallis, John D.; CrystEngComm 23 (2021) 4500–4512; doi:10.1039/D1CE00377A

data_7242940
_publ_section_title
;
 Interaction, bond formation or reaction between a dimethylamino group and
 an adjacent alkene or aldehyde group in aromatic systems controlled by
 remote molecular constraints
;
_journal_issue                   25
_journal_name_full               CrystEngComm
_journal_page_first              4500
_journal_page_last               4512
_journal_paper_doi               10.1039/D1CE00377A
_journal_volume                  23
_journal_year                    2021
_chemical_formula_moiety         'C52 H46 N4'
_chemical_formula_sum            'C52 H46 N4'
_chemical_formula_weight         726.93
_chemical_melting_point          492.5(15)
_chemical_name_systematic
;
N,N-Bis(4,5-diphenyl-8-dimethylaminonaphth-1-methylidene)-1,2-ethanediamine,
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-07-11
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-03-09 deposited with the CCDC.	2021-05-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.8042(2)
_cell_length_b                   15.4073(4)
_cell_length_c                   52.7317(11)
_cell_measurement_reflns_used    5336
_cell_measurement_temperature    150.01(10)
_cell_measurement_theta_max      70.9420
_cell_measurement_theta_min      4.7890
_cell_volume                     7965.5(3)
_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 0.998
_diffrn_measured_fraction_theta_max 0.975
_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     10.00 104.00   1.00   30.00    --   36.58  77.00 120.00   94
  2  \w    -31.00  53.00   1.00   30.00    --   36.58 -57.00 150.00   84
  3  \w     18.00  90.00   1.00   30.00    --   36.58-125.00 -30.00   72
  4  \w     17.00  71.00   1.00   30.00    --   36.58  37.00 120.00   54
  5  \w     26.00  52.00   1.00   30.00    --   36.58-125.00 -60.00   26
  6  \w    108.00 150.00   1.00  120.00    --  108.00 111.00  60.00   42
  7  \w     40.00  92.00   1.00  120.00    --  108.00-111.00-180.00   52
  8  \w     71.00 100.00   1.00  120.00    --  108.00-111.00  60.00   29
  9  \w     52.00 112.00   1.00  120.00    --  108.00-111.00 -30.00   60
 10  \w     70.00 178.00   1.00  120.00    --  108.00  15.00-150.00  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      0.1331383000
_diffrn_orient_matrix_UB_12      -0.0520931000
_diffrn_orient_matrix_UB_13      0.0029021000
_diffrn_orient_matrix_UB_21      0.0671516000
_diffrn_orient_matrix_UB_22      0.0781423000
_diffrn_orient_matrix_UB_23      0.0133146000
_diffrn_orient_matrix_UB_31      -0.0496186000
_diffrn_orient_matrix_UB_32      -0.0343106000
_diffrn_orient_matrix_UB_33      0.0258391000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0360
_diffrn_reflns_av_unetI/netI     0.0530
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       64
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_number            20439
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.131
_diffrn_reflns_theta_min         4.812
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.542
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.893
_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    1.212
_exptl_crystal_description       block
_exptl_crystal_F_000             3088
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: DCM/hexane'
_exptl_crystal_size_max          0.263
_exptl_crystal_size_mid          0.192
_exptl_crystal_size_min          0.107
_refine_diff_density_max         0.211
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     509
_refine_ls_number_reflns         7645
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0752
_refine_ls_R_factor_gt           0.0524
_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^)+(0.0577P)^2^+1.2552P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1278
_refine_ls_wR_factor_ref         0.1423
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5584
_reflns_number_total             7645
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ce00377a2.cif
_cod_data_source_block           jb426abs
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '491-494' was changed to
'492.5(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 

 Adding full bibliography for 7242927--7242944.cif.
;
_cod_database_code               7242940
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C26 H23 O2 N2'
_chemical_oxdiff_usercomment     'Yellow Block'
_reflns_odcompleteness_completeness 99.74
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C26(H26A,H26B), C27(H27A,H27B)
2.b 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), C28(H28),
  C32(H32), C33(H33), C37(H37), C38(H38), C42(H42), C43(H43), C44(H44),
 C45(H45), C46(H46), C48(H48), C49(H49), C50(H50), C51(H51), C52(H52)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C39(H39A,H39B,H39C), C40(H40A,H40B,
 H40C)
;
_shelx_res_checksum              11555
_shelx_hkl_checksum              79642
_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 1.127
_oxdiff_exptl_absorpt_empirical_full_min 0.870