Mechanofluorochromic properties of fluorescent molecules based on a dicyanomethylene-4H-pyran and indole isomer containing different alkyl chains via an alkene module
Qian, Lebin; Zhou, Yibin; Liu, Miaochang; Huang, Xiaobo; Wu, Ge; Gao, Wenxia; Ding, Jinchang; Wu, Huayue; RSC Adv. 7 (2017) 42180–; doi:10.1039/C7RA06951K

data_7229022
_publ_section_title
;
 Mechanofluorochromic properties of fluorescent molecules based on a
 dicyanomethylene-4H-pyran and indole isomer containing different alkyl
 chains via an alkene module
;
_journal_issue                   67
_journal_name_full               'RSC Adv.'
_journal_page_first              42180
_journal_paper_doi               10.1039/C7RA06951K
_journal_volume                  7
_journal_year                    2017
_chemical_formula_moiety         'C36 H34 N4 O'
_chemical_formula_sum            'C36 H34 N4 O'
_chemical_formula_weight         538.67
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-01-17
_audit_creation_method
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_audit_update_record
;
2017-06-06 deposited with the CCDC.
2017-08-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.551(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.030(3)
_cell_length_b                   21.991(3)
_cell_length_c                   9.8034(12)
_cell_measurement_reflns_used    1838
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      52.52
_cell_measurement_theta_min      2.38
_cell_volume                     4004.6(10)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_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      296
_diffrn_measured_fraction_theta_full 0.961
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0837
_diffrn_reflns_av_unetI/netI     0.1195
_diffrn_reflns_Laue_measured_fraction_full 0.961
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            22108
_diffrn_reflns_point_group_measured_fraction_full 0.961
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_theta_full        66.779
_diffrn_reflns_theta_max         66.78
_diffrn_reflns_theta_min         2.38
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.425
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.4086
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1381 before and 0.0868 after correction.
The Ratio of minimum to maximum transmission is 0.5428.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    0.893
_exptl_crystal_description       plate
_exptl_crystal_F_000             1144
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.298
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.950
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     432
_refine_ls_number_reflns         6829
_refine_ls_number_restraints     162
_refine_ls_restrained_S_all      0.953
_refine_ls_R_factor_all          0.1414
_refine_ls_R_factor_gt           0.0978
_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^)+(0.1852P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2622
_refine_ls_wR_factor_ref         0.3153
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3484
_reflns_number_total             6829
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ra06951k2.cif
_cod_data_source_block           dm17048
_cod_original_cell_volume        4004.5(9)
_cod_database_code               7229022
_shelx_estimated_absorpt_t_max   0.996
_shelx_estimated_absorpt_t_min   0.939
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
C29 \\sim C31 \\sim C31' \\sim C32' \\sim C32 \\sim C30 \\sim C30': within 2A
with sigma of 0.01 and sigma for terminal atoms of 0.02
C33 \\sim C34' \\sim C35 \\sim C36 \\sim C36' \\sim C34 \\sim C35': within 2A
with sigma of 0.01 and sigma for terminal atoms of 0.02
3. Others
 Fixed Sof: H29A(0.5) H29B(0.5) H29C(0.5) H29D(0.5) C30(0.5) H30(0.5) C31(0.5)
 H31A(0.5) H31B(0.5) H31C(0.5) C32(0.5) H32A(0.5) H32B(0.5) H32C(0.5) H33C(0.5)
 H33D(0.5) H33A(0.5) H33B(0.5) C34(0.5) H34(0.5) C35(0.5) H35A(0.5) H35B(0.5)
 H35C(0.5) C36(0.5) H36A(0.5) H36B(0.5) H36C(0.5) C30'(0.5) H30'(0.5) C31'(0.5)
 H31D(0.5) H31E(0.5) H31F(0.5) C32'(0.5) H32D(0.5) H32E(0.5) H32F(0.5)
 C34'(0.5) H34'(0.5) C35'(0.5) H35D(0.5) H35E(0.5) H35F(0.5) C36'(0.5)
 H36D(0.5) H36E(0.5) H36F(0.5)
4.a Ternary CH refined with riding coordinates:
 C30(H30), C34(H34), C30'(H30'), C34'(H34')
4.b Secondary CH2 refined with riding coordinates:
 C29(H29A,H29B), C29(H29C,H29D), C33(H33C,H33D), C33(H33A,H33B)
4.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C9(H9), C10(H10), C12(H12), C14(H14),
 C16(H16), C17(H17), C19(H19), C21(H21), C22(H22), C23(H23), C24(H24)
4.d Idealised Me refined as rotating group:
 C31(H31A,H31B,H31C), C32(H32A,H32B,H32C), C35(H35A,H35B,H35C), C36(H36A,H36B,
 H36C), C31'(H31D,H31E,H31F), C32'(H32D,H32E,H32F), C35'(H35D,H35E,H35F),
 C36'(H36D,H36E,H36F)
;
_shelx_res_checksum              49993
_shelx_fab_checksum              41038
_shelx_shelxl_version_number     2016/6
_olex2_submission_special_instructions 'No special instructions were received'