Alkylation of the K-Region in a Sterically Hindered Pyrene Carboxamide via Directed Reaction with Alkyllithiums under Air.
Ciechańska, Magdalena; Wrona-Piotrowicz, Anna; Makal, Anna; Zakrzewski, Janusz; The Journal of organic chemistry 83 (2018) 12793–12797; doi:10.1021/acs.joc.8b01024

data_4035405
_publ_section_title
;
 Alkylation of the K-Region in a Sterically Hindered Pyrene Carboxamide
 via Directed Reaction with Alkyllithiums under Air.
;
_journal_issue                   20
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12793
_journal_page_last               12797
_journal_paper_doi               10.1021/acs.joc.8b01024
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C33 H45 N O2'
_chemical_formula_sum            'C33 H45 N O2'
_chemical_formula_weight         487.70
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2016-11-28
_audit_creation_method
;
Olex2 1.2
(compiled Nov  7 2016 13:36:16 for OlexSys, GUI svn.r5261)
;
_cell_angle_alpha                90
_cell_angle_beta                 104.250(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   16.1532(6)
_cell_length_b                   19.5027(6)
_cell_length_c                   18.8925(7)
_cell_measurement_reflns_used    17233
_cell_measurement_temperature    150.11(10)
_cell_measurement_theta_max      29.7490
_cell_measurement_theta_min      1.9560
_cell_volume                     5768.6(4)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43c (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43c (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43c (Rigaku OD, 2015)'
_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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      150.11(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0013
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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     21.00 104.00   1.00   10.00    --   24.03-160.00 120.00   83
  2  \w    -47.00  48.00   1.00   10.00    --   24.03 -57.00  90.00   95
  3  \w     -8.00  98.00   1.00   10.00    --   24.03  37.00 -90.00  106
  4  \w   -104.00 -21.00   1.00   10.00    --  -24.27 160.00 120.00   83
  5  \w    -48.00  46.00   1.00   10.00    --  -24.27  57.00 -30.00   94
  6  \w    -57.00  49.00   1.00   10.00    --  -24.27  37.00-120.00  106
  7  \w    -97.00   9.00   1.00   10.00    --  -24.27 -77.00  90.00  106
  8  \w    -97.00   9.00   1.00   10.00    --  -24.27 -77.00-150.00  106
  9  \w    -97.00 -72.00   1.00   10.00    --  -24.27 -77.00 -30.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0067042000
_diffrn_orient_matrix_UB_12      -0.0215695000
_diffrn_orient_matrix_UB_13      -0.0311489000
_diffrn_orient_matrix_UB_21      -0.0409237000
_diffrn_orient_matrix_UB_22      -0.0088286000
_diffrn_orient_matrix_UB_23      0.0045622000
_diffrn_orient_matrix_UB_31      -0.0182018000
_diffrn_orient_matrix_UB_32      0.0279355000
_diffrn_orient_matrix_UB_33      -0.0225861000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71072
_diffrn_reflns_av_R_equivalents  0.0590
_diffrn_reflns_av_unetI/netI     0.0407
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            86983
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.214
_diffrn_reflns_theta_max         27.454
_diffrn_reflns_theta_min         1.666
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.068
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.443
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43c (Rigaku Oxford Diffraction, 2015)
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 colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.123
_exptl_crystal_description       block
_exptl_crystal_F_000             2128
_exptl_crystal_size_max          0.279
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.145
_refine_diff_density_max         0.261
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     681
_refine_ls_number_reflns         13198
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0781
_refine_ls_R_factor_gt           0.0584
_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^)+(0.0440P)^2^+3.3251P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1249
_refine_ls_wR_factor_ref         0.1347
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10295
_reflns_number_total             13198
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b01024_si_002.cif
_cod_data_source_block           exp_641
_cod_database_code               4035405
_shelxl_version_number           2013-2
_chemical_oxdiff_formula         'C33 H45 N O2'
_chemical_oxdiff_usercomment     'colourless needle, 100 K'
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 O42-H42 = O2-H2
 0.82 with sigma of 0.02
 N41-H41 = N1-H1
 0.86 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C3(H3), C4(H4), C43(H43), C44(H44)
3.b Secondary CH2 refined with riding coordinates:
 C22(H22A,H22B), C23(H23A,H23B), C24(H24A,H24B), C62(H62A,H62B), C63(H63A,
 H63B), C64(H64A,H64B)
3.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C8(H8), C10(H10), C11(H11), C13(H13), C46(H46), C48(H48), C50(H50),
 C51(H51), C53(H53)
3.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C25(H25A,H25B,
 H25C), C27(H27A,H27B,H27C), C28(H28A,H28B,H28C), C29(H29A,H29B,H29C), C31(H31A,
 H31B,H31C), C32(H32A,H32B,H32C), C33(H33A,H33B,H33C), C59(H59A,H59B,H59C),
 C60(H60A,H60B,H60C), C61(H61A,H61B,H61C), C65(H65A,H65B,H65C), C67(H67A,H67B,
 H67C), C68(H68A,H68B,H68C), C69(H69A,H69B,H69C), C71(H71A,H71B,H71C), C72(H72A,
 H72B,H72C), C73(H73A,H73B,H73C)
;
_olex2_date_sample_data_collection 2016-11-25
_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 1.349
_oxdiff_exptl_absorpt_empirical_full_min 0.779