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_4033796
_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_formula_moiety         'C42 H30 N4 O2, 4(H2 O)'
_chemical_formula_sum            'C42 H38 N4 O6'
_chemical_formula_weight         694.76
_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_Hall           '-P 2n 2ab'
_space_group_name_H-M_alt        'P b c n'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-04-14
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.9994(10)
_cell_length_b                   15.5034(11)
_cell_length_c                   15.4665(13)
_cell_measurement_reflns_used    7950
_cell_measurement_temperature    100
_cell_measurement_theta_max      66.8480
_cell_measurement_theta_min      4.9970
_cell_volume                     3356.8(4)
_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      100
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4685
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_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    -33.00  66.00   1.00    3.21    --   41.64 -37.00 -30.00   99
  2  \w     13.00 115.00   1.00    3.21    --   41.64  57.00 -60.00  102
  3  \w     56.00 171.00   1.00   12.84    --   92.50  22.00  80.46  115
  4  \w     19.00  96.00   1.00   12.84    --   92.50-125.00-180.00   77
  5  \w     10.00  83.00   1.00   12.84    --   92.50 -94.00  60.00   73
  6  \w     19.00  77.00   1.00   12.84    --   92.50 -45.00-120.00   58
  7  \w     10.00  83.00   1.00   12.84    --   92.50 -94.00   0.00   73
  8  \w     10.00  83.00   1.00   12.84    --   92.50 -94.00-150.00   73
  9  \w     75.00 130.00   1.00   12.84    --   92.50 -91.00 -90.65   55
 10  \w     65.00  98.00   1.00   12.84    --   92.50  30.00-150.00   33
 11  \w    115.00 145.00   1.00   12.84    --   92.50  30.00-150.00   30
 12  \w     42.00  69.00   1.00   12.84    --   92.50 -30.00-180.00   27
 13  \w     48.00  74.00   1.00   12.84    --   92.50 -77.00-150.00   26
 14  \w     67.00 130.00   1.00   12.84    --   92.50 -93.00  -0.17   63
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0078943000
_diffrn_orient_matrix_UB_12      0.0214028000
_diffrn_orient_matrix_UB_13      0.0970359000
_diffrn_orient_matrix_UB_21      0.0000839000
_diffrn_orient_matrix_UB_22      0.0971559000
_diffrn_orient_matrix_UB_23      -0.0214397000
_diffrn_orient_matrix_UB_31      -0.1096131000
_diffrn_orient_matrix_UB_32      -0.0014079000
_diffrn_orient_matrix_UB_33      -0.0070788000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0639
_diffrn_reflns_av_unetI/netI     0.0332
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            18809
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        66.905
_diffrn_reflns_theta_max         66.905
_diffrn_reflns_theta_min         4.255
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.753
_exptl_absorpt_correction_T_max  0.915
_exptl_absorpt_correction_T_min  0.841
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
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    1.375
_exptl_crystal_description       block
_exptl_crystal_F_000             1464
_exptl_crystal_size_max          0.389
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.161
_refine_diff_density_max         0.259
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         2980
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0509
_refine_ls_R_factor_gt           0.0467
_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^)+(0.0722P)^2^+1.4363P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1193
_refine_ls_wR_factor_ref         0.1243
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2688
_reflns_number_total             2980
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b01465_si_004.cif
_cod_data_source_block           jcm1398a2
_cod_database_code               4033796
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C42 H34 N4 O6'
_shelx_estimated_absorpt_t_max   0.888
_shelx_estimated_absorpt_t_min   0.758
_reflns_odcompleteness_completeness 99.29
_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, All O(H,H) groups
2. Others
 Fixed Sof: O3A(0.5) H3AA(0.5) H3AB(0.5) O3B(0.5) H3BA(0.5) H3BB(0.5)
3.a Free rotating group:
 O2(H2A,H2B), O3A(H3AA,H3AB), O3B(H3BA,H3BB)
3.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C7(H7A,H7B)
3.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C9(H9), C11(H11), C12(H12), C14(H14), C15(H15), C16(H16)
3.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_shelx_res_checksum              33263
_shelx_hkl_checksum              94197
_olex2_date_sample_data_collection 2014-11-10
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a nylon loop in perfluoroether oil'
_olex2_submission_original_sample_id JCM1398A1
_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 1.615
_oxdiff_exptl_absorpt_empirical_full_min 0.726