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_7242936
_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_absolute_configuration unk
_chemical_formula_moiety         'C18 H19 N O'
_chemical_formula_sum            'C18 H19 N O'
_chemical_formula_weight         265.34
_chemical_melting_point          354.5(15)
_chemical_name_systematic
;
4-(dimethylamino)-9,9-dimethyl-9H-fluorene-5-carbaldehyde
;
_space_group_crystal_system      tetragonal
_space_group_IT_number           110
_space_group_name_Hall           'I 4bw -2c'
_space_group_name_H-M_alt        'I 41 c d'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2019-09-16
_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            16
_cell_length_a                   24.79560(10)
_cell_length_b                   24.79560(10)
_cell_length_c                   9.47440(10)
_cell_measurement_reflns_used    7029
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      71.9580
_cell_measurement_theta_min      5.0360
_cell_volume                     5825.07(7)
_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      149.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9832
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_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   -101.00 -17.00   1.00   25.00    --  -33.50 -57.00  90.00   84
  2  \w     20.00 104.00   1.00   25.00    --   36.58  57.00-180.00   84
  3  \w    -30.00  57.00   1.00   25.00    --   36.58 -65.00 -62.50   87
  4  \w     91.00 176.00   1.00  100.00    --  108.00  45.00-180.00   85
  5  \w     42.00 128.00   1.00  100.00    --  108.00 -65.00  96.86   86
  6  \w     91.00 176.00   1.00  100.00    --  108.00  45.00-150.00   85
  7  \w     41.00 126.00   1.00  100.00    --  108.00 -61.00-180.00   85
  8  \w     87.00 178.00   1.00  100.00    --  108.00  30.00 120.00   91
  9  \w     40.00 125.00   1.00  100.00    --  108.00 -45.00  30.00   85
 10  \w     91.00 176.00   1.00  100.00    --  108.00  45.00 -90.00   85
 11  \w     42.00 128.00   1.00  100.00    --  108.00 -65.00 -90.13   86
 12  \w    -30.00   1.00   1.00   25.00    --   36.58 -61.00 164.14   31
 13  \w     18.00 103.00   1.00   25.00    --   36.58  63.00 -62.16   85
;
_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      0.0220384000
_diffrn_orient_matrix_UB_12      0.0571186000
_diffrn_orient_matrix_UB_13      -0.0281965000
_diffrn_orient_matrix_UB_21      0.0580414000
_diffrn_orient_matrix_UB_22      -0.0210297000
_diffrn_orient_matrix_UB_23      0.0189763000
_diffrn_orient_matrix_UB_31      0.0029645000
_diffrn_orient_matrix_UB_32      -0.0126256000
_diffrn_orient_matrix_UB_33      -0.1588578000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0321
_diffrn_reflns_av_unetI/netI     0.0207
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            13777
_diffrn_reflns_point_group_measured_fraction_full 0.837
_diffrn_reflns_point_group_measured_fraction_max 0.837
_diffrn_reflns_theta_full        66.548
_diffrn_reflns_theta_max         66.548
_diffrn_reflns_theta_min         3.565
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.579
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.897
_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            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.210
_exptl_crystal_description       block
_exptl_crystal_F_000             2272
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: DCM/hexane'
_exptl_crystal_size_max          0.286
_exptl_crystal_size_mid          0.135
_exptl_crystal_size_min          0.099
_refine_diff_density_max         0.128
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details
;
 Flack x determined using 739 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.27(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         2152
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0322
_refine_ls_R_factor_gt           0.0314
_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^)+(0.0488P)^2^+1.3486P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0797
_refine_ls_wR_factor_ref         0.0803
_reflns_Friedel_coverage         0.581
_reflns_Friedel_fraction_full    0.661
_reflns_Friedel_fraction_max     0.661
_reflns_number_gt                2108
_reflns_number_total             2152
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ce00377a2.cif
_cod_data_source_block           jb286abs
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '353-356' was changed to
'354.5(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_original_cell_volume        5825.07(8)
_cod_database_code               7242936
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C18 N1 O1 H19'
_chemical_oxdiff_usercomment     'Yellow Needle'
_shelx_estimated_absorpt_t_max   0.945
_shelx_estimated_absorpt_t_min   0.852
_reflns_odcompleteness_completeness 96.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     72.65
_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:
 C18(H18), C2(H2), C4(H4), C11(H11), C3(H3), C10(H10), C9(H9)
2.b Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C14(H14A,H14B,
 H14C)
;
_shelx_res_checksum              89212
_shelx_hkl_checksum              20222
_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 1.204
_oxdiff_exptl_absorpt_empirical_full_min 0.901