Modulation of Chiroptical Properties in a Series of Helicene-like Compounds.
Guy, Laure; Mosser, Maëlle; Pitrat, Delphine; Mulatier, Jean-Christophe; Kukułka, Mercedes; Srebro-Hooper, Monika; Jeanneau, Erwann; Bensalah-Ledoux, Amina; Baguenard, Bruno; Guy, Stéphan; The Journal of organic chemistry 84 (2019) 10870–10876; doi:10.1021/acs.joc.9b01465

data_4033797
_publ_section_title
;
 Modulation of Chiroptical Properties in a Series of Helicene-like
 Compounds.
;
_journal_issue                   17
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              10870
_journal_page_last               10876
_journal_paper_doi               10.1021/acs.joc.9b01465
_journal_volume                  84
_journal_year                    2019
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C41 H26 N4 O2, H2 O'
_chemical_formula_sum            'C41 H28 N4 O3'
_chemical_formula_weight         624.67
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-04-04
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 106.253(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.9280(2)
_cell_length_b                   12.6925(2)
_cell_length_c                   11.1940(2)
_cell_measurement_reflns_used    9156
_cell_measurement_temperature    150
_cell_measurement_theta_max      28.3450
_cell_measurement_theta_min      3.7460
_cell_volume                     1490.60(5)
_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_temperature      150
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9897
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.900
_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    -55.00  46.00   1.00   45.00    --   16.67 -19.00  60.00  101
  2  \w      0.00  84.00   1.00   45.00    --   16.67  57.00 -90.00   84
  3  \w    -53.00  86.00   1.00   45.00    --   16.67   0.00 -90.00  139
  4  \w    -53.00  86.00   1.00   45.00    --   16.67   0.00 150.00  139
  5  \w    -20.00  25.00   1.00   45.00    --  -14.17 -99.00 120.00   45
  6  \w    -20.00  25.00   1.00   45.00    --  -14.17 -99.00 -60.00   45
  7  \w    -20.00  56.00   1.00   45.00    --   16.67 -99.00  60.00   76
  8  \w    -20.00  18.00   1.00   45.00    --   16.67 -99.00-180.00   38
  9  \w    -20.00  56.00   1.00   45.00    --   16.67 -99.00 -60.00   76
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Nova'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0207925000
_diffrn_orient_matrix_UB_12      -0.0178659000
_diffrn_orient_matrix_UB_13      -0.0511200000
_diffrn_orient_matrix_UB_21      0.0389638000
_diffrn_orient_matrix_UB_22      -0.0383668000
_diffrn_orient_matrix_UB_23      0.0386828000
_diffrn_orient_matrix_UB_31      -0.0511857000
_diffrn_orient_matrix_UB_32      -0.0364934000
_diffrn_orient_matrix_UB_33      -0.0157051000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0354
_diffrn_reflns_av_unetI/netI     0.0457
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.900
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            26463
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.867
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.636
_diffrn_reflns_theta_min         3.464
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Mova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.925
_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    1.392
_exptl_crystal_description       needle
_exptl_crystal_F_000             652
_exptl_crystal_size_max          0.091
_exptl_crystal_size_mid          0.082
_exptl_crystal_size_min          0.035
_refine_diff_density_max         0.175
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details
;
 Flack x determined using 2253 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.6(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     436
_refine_ls_number_reflns         7299
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0609
_refine_ls_R_factor_gt           0.0453
_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^)+(0.0340P)^2^+0.1297P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0801
_refine_ls_wR_factor_ref         0.0866
_reflns_Friedel_coverage         0.847
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.830
_reflns_number_gt                6015
_reflns_number_total             7299
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b01465_si_002.cif
_cod_data_source_block           heli5
_cod_database_code               4033797
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C41 H28 N4 O3'
_reflns_odcompleteness_completeness 99.72
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 O(H,H) groups
2.a Free rotating group:
 O3(H3A,H3B)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C6(H6A,H6B), C7(H7A,H7B), C36(H36A,H36B), C37(H37A,H37B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C9(H9), C11(H11), C12(H12), C14(H14), C15(H15), C16(H16),
 C27(H27), C28(H28), C29(H29), C31(H31), C32(H32), C34(H34), C39(H39), C40(H40)
;
_shelx_res_checksum              99883
_shelx_hkl_checksum              16227
_olex2_date_sample_data_collection 2019-03-19
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a Nylon loop in perfluoroether oil'
_olex2_submission_original_sample_id Heli5
_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 1.223
_oxdiff_exptl_absorpt_empirical_full_min 0.854