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_1558426
_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 H20'
_chemical_formula_sum            'C34 H20'
_chemical_formula_weight         428.50
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2018-12-11
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-01-03 deposited with the CCDC.	2020-06-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.758(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   11.0876(3)
_cell_length_b                   20.5912(4)
_cell_length_c                   19.1254(4)
_cell_measurement_reflns_used    5061
_cell_measurement_temperature    150
_cell_measurement_theta_max      72.5240
_cell_measurement_theta_min      4.2930
_cell_volume                     4336.12(17)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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      150
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_details
;
  1 omega  -31.00   53.00   1.0000    1.1500
omega____ theta____ kappa____ phi______ frames
    -       36.5421  -57.0000 -150.0000 84

  2 omega  -35.00   66.00   1.0000    1.1500
omega____ theta____ kappa____ phi______ frames
    -       36.5421  -19.0000    0.0000 101

  3 omega   10.00  104.00   1.0000    1.1500
omega____ theta____ kappa____ phi______ frames
    -       36.5421   77.0000  150.0000 94

  4 omega    1.00   75.00   1.0000    1.1500
omega____ theta____ kappa____ phi______ frames
    -       36.5421  -99.0000  150.0000 74

  5 omega   23.00   90.00   1.0000    1.1500
omega____ theta____ kappa____ phi______ frames
    -       36.5421 -125.0000  120.0000 67

  6 omega  -35.00   66.00   1.0000    1.1500
omega____ theta____ kappa____ phi______ frames
    -       36.5421  -19.0000 -150.0000 101

  7 omega   38.00   91.00   1.0000    4.5900
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  120.0000 53

  8 omega   40.00   98.00   1.0000    4.5900
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -30.0000 58

  9 omega   38.00   91.00   1.0000    4.5900
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000    0.0000 53

 10 omega   38.00   91.00   1.0000    4.5900
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  150.0000 53

 11 omega   38.00   91.00   1.0000    4.5900
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -180.0000 53

 12 omega   91.00  176.00   1.0000    4.5900
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000   60.0000 85

 13 omega   90.00  175.00   1.0000    4.5900
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  -60.0000 85

 14 omega   40.00   98.00   1.0000    4.5900
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -60.0000 58

 15 omega   87.00  178.00   1.0000    4.5900
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000    0.0000 91

 16 omega   10.00   72.00   1.0000    1.1500
omega____ theta____ kappa____ phi______ frames
    -       36.5421   77.0000  -90.0000 62

 17 omega   20.00   95.00   1.0000    1.1500
omega____ theta____ kappa____ phi______ frames
    -       36.5421   57.0000    0.0000 75
;
_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_UB_11      0.0628457000
_diffrn_orient_matrix_UB_12      0.0426698000
_diffrn_orient_matrix_UB_13      -0.0511025000
_diffrn_orient_matrix_UB_21      -0.1248756000
_diffrn_orient_matrix_UB_22      0.0197630000
_diffrn_orient_matrix_UB_23      -0.0379892000
_diffrn_orient_matrix_UB_31      -0.0036577000
_diffrn_orient_matrix_UB_32      0.0582288000
_diffrn_orient_matrix_UB_33      0.0502807000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0382
_diffrn_reflns_av_unetI/netI     0.0420
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12071
_diffrn_reflns_point_group_measured_fraction_full 0.712
_diffrn_reflns_point_group_measured_fraction_max 0.687
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.710
_diffrn_reflns_theta_min         4.554
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.566
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58428
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear orangish orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   orangish
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_description       block
_exptl_crystal_F_000             1792
_exptl_crystal_size_max          0.65
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.588
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details
;
 Flack x determined using 1436 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     613
_refine_ls_number_reflns         5939
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0534
_refine_ls_R_factor_gt           0.0505
_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^)+(0.0974P)^2^+0.4671P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1342
_refine_ls_wR_factor_ref         0.1392
_reflns_Friedel_coverage         0.402
_reflns_Friedel_fraction_full    0.423
_reflns_Friedel_fraction_max     0.395
_reflns_number_gt                5529
_reflns_number_total             5939
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0sc02058c2.cif
_cod_data_source_block           zfl-d5-150k
_cod_original_cell_volume        4336.13(17)
_cod_database_code               1558426
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 99.90
_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:
 C005(H005), C007(H007), C008(H008), C00A(H00A), C00C(H00C), C00I(H00I),
 C00J(H00J), C00K(H00K), C00N(H00N), C00S(H00S), C00U(H00U), C00W(H00W),
 C00Z(H00Z), C011(H011), C012(H012), C013(H013), C014(H014), C016(H016),
 C017(H017), C018(H018), C019(H019), C01B(H01B), C01D(H01D), C01E(H01E),
 C01G(H01G), C01H(H01H), C01I(H01I), C01J(H01J), C01K(H01K), C01L(H01L),
 C01M(H01M), C01N(H01N), C01O(H01O), C01P(H01P), C01R(H01R), C01S(H01S),
 C01T(H01T), C01U(H01U), C01V(H01V), C01W(H01W)
;
_olex2_submission_special_instructions 'No special instructions were received'