Structure-function relationships of donor-acceptor Stenhouse adduct photochromic switches.
Mallo, Neil; Foley, Eric D.; Iranmanesh, Hasti; Kennedy, Aaron D. W.; Luis, Ena T.; Ho, Junming; Harper, Jason B.; Beves, Jonathon E.; Chemical science 9 (2018) 8242–8252; doi:10.1039/c8sc03218a

data_1549929
_publ_section_title
;
 Structure-function relationships of donor-acceptor Stenhouse adduct
 photochromic switches.
;
_journal_issue                   43
_journal_name_full               'Chemical science'
_journal_page_first              8242
_journal_page_last               8252
_journal_paper_doi               10.1039/c8sc03218a
_journal_volume                  9
_journal_year                    2018
_chemical_formula_moiety         'C15 H19 N3 O4, 0.5(C H2 Cl2), 0.56(H2 O)'
_chemical_formula_sum            'C15.5 H20.27 Cl N3 O4.64'
_chemical_formula_weight         358.23
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2018-04-19
_audit_creation_method
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2018-04-24 deposited with the CCDC.
2018-08-29 downloaded from the CCDC.
;
_cell_angle_alpha                89.03(3)
_cell_angle_beta                 85.92(3)
_cell_angle_gamma                75.68(3)
_cell_formula_units_Z            4
_cell_length_a                   10.420(2)
_cell_length_b                   13.200(3)
_cell_length_c                   13.900(3)
_cell_measurement_reflns_used    10155
_cell_measurement_temperature    100
_cell_measurement_theta_max      29.57
_cell_measurement_theta_min      1.469
_cell_volume                     1847.8(7)
_computing_cell_refinement       'XDS (Kabsch, 1993)'
_computing_data_collection       'BluIce (McPhillips, 2002)'
_computing_data_reduction        'XDS (Kabsch, 1993)'
_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      100
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  MX1
_diffrn_measurement_method       'Phi Scan'
_diffrn_radiation_monochromator  'Silicon Double Crystal'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0456
_diffrn_reflns_av_unetI/netI     0.0271
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            61226
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.271
_diffrn_reflns_theta_min         1.469
_diffrn_source                   'MX1 Beamline Australian Synchrotron'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.233
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_description       plate
_exptl_crystal_F_000             753
_exptl_crystal_size_max          0.9
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.01
_refine_diff_density_max         2.362
_refine_diff_density_min         -0.949
_refine_diff_density_rms         0.125
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     465
_refine_ls_number_reflns         9130
_refine_ls_number_restraints     43
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.1089
_refine_ls_R_factor_gt           0.0935
_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^)+(0.1886P)^2^+2.1259P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2851
_refine_ls_wR_factor_ref         0.3019
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7177
_reflns_number_total             9130
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8sc03218a2.cif
_cod_data_source_block           12b
_cod_depositor_comments
'Adding full bibliography for 1549921--1549929.cif.'
_cod_original_cell_volume        1847.7(7)
_cod_original_formula_sum        'C15.50 H20.27 Cl N3 O4.64'
_cod_database_code               1549929
_shelx_shelxl_version_number     2016/6
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2. Rigid bond restraints
 C14, C15
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
C15 \\sim C14: within 1.7A with sigma of 0.005 and sigma for terminal atoms of
0.08
C13 \\sim C12: within 1.7A with sigma of 0.004 and sigma for terminal atoms of
0.08
Uanis(N3) \\sim Ueq, Uanis(C15) \\sim Ueq, Uanis(C14) \\sim Ueq, Uanis(C13)
\\sim Ueq, Uanis(C12) \\sim Ueq: with sigma of 0.01 and sigma for terminal
atoms of 0.2
Uanis(C14) \\sim Ueq, Uanis(C13) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.2
4. Others
 Sof(H31C)=Sof(H31D)=Sof(Cl1A)=Sof(Cl2A)=1-FVAR(1)
 Sof(H31A)=Sof(H31B)=Sof(Cl2)=Sof(Cl1)=FVAR(1)
 Fixed Sof: O10(0.64691) H10A(0.64691) H10B(0.64691) O9(0.46361) H9A(0.46361)
 H9B(0.46361)
5.a Riding coordinates:
 O10(H10A,H10B), O9(H9A,H9B)
5.b Ternary CH refined with riding coordinates:
 N3(H3), N6(H6), C22(H22), C11(H11), C7(H7), C26(H26)
5.c Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C27(H27A,H27B), C15(H15A,H15B), C30(H30A,H30B), C31(H31A,
 H31B), C31(H31C,H31D), C28(H28A,H28B), C13(H13A,H13B), C29(H29A,H29B),
 C14(H14A,H14B)
5.d Aromatic/amide H refined with riding coordinates:
 C10(H10), C9(H9), C25(H25), C24(H24)
5.e Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C17(H17A,H17B,H17C), C3(H3A,H3B,H3C), C18(H18A,H18B,H18C)
;
_shelx_res_checksum              92067
_olex2_submission_special_instructions 'No special instructions were received'