Molecular engineering enabling reversible transformation between helical and planar conformations by cyclization of alkynes.
Yan, Lipeng; Ma, Weixin; Lan, Jingbo; Cheng, Hu; Bin, Zhengyang; Wu, Di; You, Jingsong; Chemical science 12 (2020) 2419–2426; doi:10.1039/d0sc05844k

data_1559735
_publ_section_title
;
 Molecular engineering enabling reversible transformation between helical
 and planar conformations by cyclization of alkynes.
;
_journal_issue                   7
_journal_name_full               'Chemical science'
_journal_page_first              2419
_journal_page_last               2426
_journal_paper_doi               10.1039/d0sc05844k
_journal_volume                  12
_journal_year                    2020
_chemical_formula_moiety         'Cl, 4(H2 O), C39 H27 N2'
_chemical_formula_sum            'C39 H35 Cl N2 O4'
_chemical_formula_weight         631.14
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2016-11-18
_audit_creation_method
;
Olex2 1.2
(compiled 2016.11.07 svn.r3352 for OlexSys, GUI svn.r5261)
;
_audit_update_record
;
2020-09-27 deposited with the CCDC.	2020-12-03 downloaded from the CCDC.
;
_cell_angle_alpha                76.950(3)
_cell_angle_beta                 80.721(3)
_cell_angle_gamma                83.880(3)
_cell_formula_units_Z            2
_cell_length_a                   7.0556(3)
_cell_length_b                   11.2701(4)
_cell_length_c                   21.8311(8)
_cell_measurement_reflns_used    8175
_cell_measurement_temperature    293.1(6)
_cell_measurement_theta_max      72.4630
_cell_measurement_theta_min      4.9400
_cell_volume                     1664.53(11)
_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      293.1(6)
_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    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -57.0000  -60.0000 84

  2 omega  -33.00   55.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -38.0000    0.0000 88

  3 omega    1.00   75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -99.0000   60.0000 74

  4 omega   10.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   77.0000    0.0000 94

  5 omega  -31.00   63.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -77.0000  -60.0000 94

  6 omega   23.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921 -125.0000 -180.0000 67

  7 omega    7.00  108.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   19.0000 -180.0000 101

  8 omega   20.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   57.0000 -120.0000 84

  9 omega   29.00   96.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921 -135.0000  -37.0000 67

 10 omega   40.00   98.00   1.0000    3.0800
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -120.0000 58

 11 omega   40.00   98.00   1.0000    3.0800
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -30.0000 58

 12 omega   57.00  150.00   1.0000    3.0800
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000  -30.0000 93

 13 omega   39.00  109.00   1.0000    3.0800
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   90.0000 70

 14 omega   70.00  178.00   1.0000    3.0800
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000  150.0000 108

 15 omega   70.00  178.00   1.0000    3.0800
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000   60.0000 108

 16 omega   40.00   98.00   1.0000    3.0800
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   60.0000 58

 17 omega   39.00  109.00   1.0000    3.0800
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000    0.0000 70

 18 omega   40.00   98.00   1.0000    3.0800
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -60.0000 58

 19 omega   91.00  176.00   1.0000    3.0800
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  -60.0000 85

 20 omega   40.00   98.00   1.0000    3.0800
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000    0.0000 58

 21 omega   39.00  109.00   1.0000    3.0800
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -90.0000 70

 22 omega   38.00   91.00   1.0000    3.0800
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  120.0000 53

 23 omega   40.00   98.00   1.0000    3.0800
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -180.0000 58

 24 omega   38.00  116.00   1.0000    3.0800
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -150.0000 78

 25 omega   10.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   77.0000  150.0000 94

 26 omega  -33.00   55.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -38.0000  150.0000 88

 27 omega  -31.00   53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -57.0000   90.0000 84

 28 omega   10.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   77.0000 -150.0000 94

 29 omega   20.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   57.0000   60.0000 84

 30 omega   10.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   77.0000   90.0000 94

 31 omega   10.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   77.0000   60.0000 94

 32 omega    7.00  108.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   19.0000  -60.0000 101

 33 omega  -31.00   53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -57.0000 -150.0000 84

 34 omega   17.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   38.0000  -30.0000 88

 35 omega   10.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   77.0000  -90.0000 94

 36 omega   81.00  176.00   1.0000    3.0800
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -120.0000 95
;
_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      0.0464888000
_diffrn_orient_matrix_UB_12      0.0299334000
_diffrn_orient_matrix_UB_13      -0.0729985000
_diffrn_orient_matrix_UB_21      0.2076819000
_diffrn_orient_matrix_UB_22      0.0231697000
_diffrn_orient_matrix_UB_23      0.0050072000
_diffrn_orient_matrix_UB_31      0.0626048000
_diffrn_orient_matrix_UB_32      -0.1355063000
_diffrn_orient_matrix_UB_33      0.0008818000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0408
_diffrn_reflns_av_unetI/netI     0.0282
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            21394
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.696
_diffrn_reflns_theta_min         4.136
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.361
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.51283
_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 light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.259
_exptl_crystal_description       plate
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.75
_exptl_crystal_size_mid          0.65
_exptl_crystal_size_min          0.35
_refine_diff_density_max         0.375
_refine_diff_density_min         -0.330
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     427
_refine_ls_number_reflns         6486
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0643
_refine_ls_R_factor_gt           0.0573
_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^)+(0.1150P)^2^+0.2320P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1664
_refine_ls_wR_factor_ref         0.1771
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5472
_reflns_number_total             6486
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0sc05844k2.cif
_cod_data_source_block           ylp-acid
_cod_depositor_comments
;Adding full bibliography for 1559735--1559736.cif.

 Adding full bibliography for 1559735--1559736.cif.
;
_cod_database_code               1559735
_reflns_odcompleteness_completeness 99.95
_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 N(H) groups
 At 1.5 times of:
  All O(H,H) groups
2.a Free rotating group:
 O002(H00A,H00B), O005(H00C,H00D), O006(H00E,H00F), O007(H00G,H00H)
2.b Aromatic/amide H refined with riding coordinates:
 N004(H004), C00I(H00I), C00M(H00M), C00N(H00N), C00O(H00O), C00P(H00P),
 C00Q(H00Q), C00R(H00R), C00S(H00S), C00T(H00T), C00U(H00U), C00V(H00V),
 C00W(H00W), C00X(H00X), C00Y(H00Y), C00Z(H00Z), C010(H010), C011(H011),
 C012(H012), C013(H013), C014(H014), C015(H015), C016(H016), C017(H017),
 C018(H018), C019(H019), C01A(H01A)
;
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2016-11-18
_olex2_submission_special_instructions 'No special instructions were received'