Build-Up of Double Carbohelicenes Using Nitroarenes: Dual Role of the Nitro Functionality as Activation and Leaving Group
Zhou, Fulin; Zhou, Fujian; Su, Rongchuan; Yang, Yudong; You, Jingsong; Chemical Science  (2020) –; doi:10.1039/D0SC02058C

data_1558427
_publ_section_title
;
 Build-Up of Double Carbohelicenes Using Nitroarenes: Dual Role of the
 Nitro Functionality as Activation and Leaving Group
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D0SC02058C
_journal_year                    2020
_chemical_formula_moiety         'C34 H18'
_chemical_formula_sum            'C34 H18'
_chemical_formula_weight         426.48
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_Hall           '-P 2ac 2n'
_space_group_name_H-M_alt        'P n m a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2018-12-24
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2020-01-03 deposited with the CCDC.	2020-06-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.8468(6)
_cell_length_b                   23.408(2)
_cell_length_c                   11.3681(9)
_cell_measurement_reflns_used    1906
_cell_measurement_temperature    292.2(5)
_cell_measurement_theta_max      72.0090
_cell_measurement_theta_min      4.2640
_cell_volume                     2088.1(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      292.2(5)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.973
_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    -53.00  31.00   1.00    2.52    --  -36.29  57.00  90.00   84
  2  \w   -104.00 -20.00   1.00    2.52    --  -36.29 -57.00 -30.00   84
  3  \w    -31.00  63.00   1.00    2.52    --   36.29 -77.00-120.00   94
  4  \w     23.00  90.00   1.00    2.52    --   36.29-125.00-120.00   67
  5  \w     39.00 109.00   1.00   10.10    --  108.71 -94.00 150.00   70
  6  \w     42.00 127.00   1.00   10.10    --  108.71 -61.00-120.00   85
  7  \w     40.00 126.00   1.00   10.10    --  108.71 -45.00 -30.00   86
  8  \w    100.00 150.00   1.00   10.10    --  108.71 111.00 150.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0576150000
_diffrn_orient_matrix_UB_12      0.0628105000
_diffrn_orient_matrix_UB_13      0.0113578000
_diffrn_orient_matrix_UB_21      0.1568103000
_diffrn_orient_matrix_UB_22      0.0130501000
_diffrn_orient_matrix_UB_23      0.0771729000
_diffrn_orient_matrix_UB_31      0.1032045000
_diffrn_orient_matrix_UB_32      0.0150005000
_diffrn_orient_matrix_UB_33      -0.1106268000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0329
_diffrn_reflns_av_unetI/netI     0.0315
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5041
_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        67.032
_diffrn_reflns_theta_max         67.032
_diffrn_reflns_theta_min         3.777
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.588
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80684
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_description       block
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.165
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.144
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         1863
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.144
_refine_ls_R_factor_all          0.0920
_refine_ls_R_factor_gt           0.0820
_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^)+(0.0794P)^2^+1.7193P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2225
_refine_ls_wR_factor_ref         0.2300
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1521
_reflns_number_total             1863
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0sc02058c2.cif
_cod_data_source_block           zfl-5-2
_cod_original_cell_volume        2088.0(3)
_cod_database_code               1558427
_reflns_odcompleteness_completeness 97.39
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C009(H009), C00A(H00A), C00B(H00B), C00C(H00C), C00D(H00D), C00E(H00E),
 C00F(H00F), C00G(H00G), C00H(H00H)
;
_shelx_res_checksum              48844
_shelx_hkl_checksum              94087
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2018-12-24
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.483
_oxdiff_exptl_absorpt_empirical_full_min 0.694