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_7242943
_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         'C25 H22 N O, C3 H3 O4'
_chemical_formula_sum            'C28 H25 N O5'
_chemical_formula_weight         455.49
_chemical_melting_point          442.5(15)
_chemical_name_systematic
;
2-hydroxy-1,1-dimethyl-5,6-diphenyl-1,2-dihydrobenzo[cd]indol-1-ium monomalonate,
;
_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             2019-09-25
_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                67.400(5)
_cell_angle_beta                 86.108(4)
_cell_angle_gamma                81.742(4)
_cell_formula_units_Z            2
_cell_length_a                   6.0395(3)
_cell_length_b                   13.8019(8)
_cell_length_c                   14.6137(9)
_cell_measurement_reflns_used    5015
_cell_measurement_temperature    150.01(10)
_cell_measurement_theta_max      30.2800
_cell_measurement_theta_min      3.5580
_cell_volume                     1112.84(12)
_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 0.904
_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    -86.00   0.00   1.00   35.00    --  -19.97 -65.00-139.19   86
  2  \w    -86.00   0.00   1.00   35.00    --  -19.97 -65.00  95.48   86
  3  \w    -87.00   0.00   1.00   35.00    --  -19.97 -64.00 166.72   87
  4  \w      1.00  87.00   1.00   35.00    --   20.05  63.00 179.03   86
  5  \w    -51.00  49.00   1.00   35.00    --   20.05 -19.00 -90.00  100
  6  \w    -47.00  36.00   1.00   35.00    --   20.05 -55.00-139.48   83
  7  \w      3.00  87.00   1.00   35.00    --   20.05  57.00   0.00   84
  8  \f     62.00 101.00   1.00   35.00  20.05  20.05  40.00    --    39
  9  \w      0.00  87.00   1.00   35.00    --   20.05  65.00  81.02   87
 10  \w    -47.00   8.00   1.00   35.00    --   20.05 -63.00 151.56   55
 11  \w    -46.00  40.00   1.00   35.00    --   20.05 -65.00  78.71   86
;
_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      -0.0511286000
_diffrn_orient_matrix_UB_12      -0.0471413000
_diffrn_orient_matrix_UB_13      0.0193553000
_diffrn_orient_matrix_UB_21      0.1039004000
_diffrn_orient_matrix_UB_22      -0.0292785000
_diffrn_orient_matrix_UB_23      0.0198735000
_diffrn_orient_matrix_UB_31      -0.0260134000
_diffrn_orient_matrix_UB_32      0.0083935000
_diffrn_orient_matrix_UB_33      0.0446647000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0533
_diffrn_reflns_av_unetI/netI     0.0685
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.904
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            23808
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.904
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.889
_diffrn_reflns_theta_min         3.224
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.968
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_description       plate
_exptl_crystal_F_000             480
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: ethyl acetate / DCM'
_exptl_crystal_size_max          0.193
_exptl_crystal_size_mid          0.138
_exptl_crystal_size_min          0.055
_refine_diff_density_max         0.441
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     311
_refine_ls_number_reflns         6361
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.1127
_refine_ls_R_factor_gt           0.0644
_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^)+(0.0545P)^2^+0.5012P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1326
_refine_ls_wR_factor_ref         0.1563
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4061
_reflns_number_total             6361
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ce00377a2.cif
_cod_data_source_block           sy149abs
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '441-444' was changed to
'442.5(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               7242943
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C25 O2 N1 H21'
_chemical_oxdiff_usercomment     'Colourless plate'
_reflns_odcompleteness_completeness 99.78
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.22
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C25(H25)
2.b Secondary CH2 refined with riding coordinates:
 C27(H27A,H27B)
2.c 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)
2.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1), O4(H4)
;
_shelx_res_checksum              66234
_shelx_hkl_checksum              60813
_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 1.103
_oxdiff_exptl_absorpt_empirical_full_min 0.918