Macrocyclic Enforcement of Twist in Secondary Amide: Reactivity and Influence on Photoisomerisation
Pathak, Dibyajyoti; Srivastava, Aasheesh; Chemical Communications  (2022) –; doi:10.1039/D2CC04780B

data_7130847
_publ_section_title
;
 Macrocyclic Enforcement of Twist in Secondary Amide: Reactivity and
 Influence on Photoisomerisation
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC04780B
_journal_year                    2022
_chemical_formula_moiety         'C19 H17 N5 O2'
_chemical_formula_sum            'C19 H17 N5 O2'
_chemical_formula_weight         347.38
_chemical_name_common            RedcDP2
_chemical_name_systematic        ReducedcycloDiazoP2
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2022-08-22
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-08-22 deposited with the CCDC.	2022-10-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.013(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.3311(6)
_cell_length_b                   18.0936(9)
_cell_length_c                   8.8295(4)
_cell_measurement_reflns_used    7746
_cell_measurement_temperature    140.0
_cell_measurement_theta_max      29.75
_cell_measurement_theta_min      2.25
_cell_volume                     1638.12(15)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      140.0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-III CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1038
_diffrn_reflns_av_unetI/netI     0.0895
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            32357
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.091
_diffrn_reflns_theta_min         2.283
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.6927
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1050 before and 0.0638 after correction.
The Ratio of minimum to maximum transmission is 0.9286.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_description       plate
_exptl_crystal_F_000             728
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Chloroform/Ethylacetate'
_refine_diff_density_max         0.366
_refine_diff_density_min         -0.431
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     240
_refine_ls_number_reflns         4817
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.1460
_refine_ls_R_factor_gt           0.0779
_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^)+(0.0408P)^2^+1.8860P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1309
_refine_ls_wR_factor_ref         0.1523
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2965
_reflns_number_total             4817
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc04780b2.cif
_cod_data_source_block           d1_a
_cod_database_code               7130847
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All N(H,H) groups
2.a Rotating group:
 N5(H5A,H5B)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B)
2.c Aromatic/amide H refined with riding coordinates:
 N2(H2A), C9(H9), C15(H15), C18(H18), C4(H4), C12(H12), C2(H2B), C10(H10),
 C3(H3), C11(H11), C16(H16), C17(H17)
;
_shelx_res_checksum              63683
_shelx_hkl_checksum              42689
_olex2_submission_special_instructions 'No special instructions were received'