Photo-induced living radical polymerization of acrylates utilizing a discrete copper(II)-formate complex
Athina Anastasaki; Vasiliki Nikolaou; Francesca Brandford-Adams; Gabit Nurumbetov; Qiang Zhang; Guy J. Clarkson; David J. Fox; Paul Wilson; Kristian Kempe; David M. Haddleton; Chem.Commun. 51 (2015) 5626–; doi:10.1039/C4cc09916H

data_7116795
_publ_section_title
;
 Photo-induced living radical polymerization of acrylates utilizing a
 discrete copper(II)-formate complex
;
_journal_name_full               Chem.Commun.
_journal_page_first              5626
_journal_paper_doi               10.1039/C4cc09916H
_journal_volume                  51
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C13 H31 Cu N4 O2, Cl O4'
_chemical_formula_sum            'C13 H31 Cl Cu N4 O6'
_chemical_formula_weight         438.41
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2014-09-21
_audit_creation_method
;
Olex2 1.2
(compiled 2014.08.28 svn.r2986 for OlexSys, GUI svn.r4874)
;
_audit_update_record
;
2014-12-11 deposited with the CCDC.
2015-01-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.0837(7)
_cell_length_b                   12.5402(5)
_cell_length_c                   9.2795(8)
_cell_measurement_reflns_used    2373
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      29.0920
_cell_measurement_theta_min      2.9820
_cell_volume                     1988.0(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      180(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.2833
_diffrn_detector_type            Ruby
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.895
_diffrn_measurement_details
;
  1 omega  -65.00   47.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       13.4718  -77.0000   60.0000 112

  2 omega  -22.00    9.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.2530  -99.0000  -60.0000 31
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0446355000
_diffrn_orient_matrix_UB_12      0.0111964000
_diffrn_orient_matrix_UB_13      -0.0433144000
_diffrn_orient_matrix_UB_21      0.0461912000
_diffrn_orient_matrix_UB_22      -0.0321808000
_diffrn_orient_matrix_UB_23      0.0106593000
_diffrn_orient_matrix_UB_31      -0.0415013000
_diffrn_orient_matrix_UB_32      -0.0237330000
_diffrn_orient_matrix_UB_33      -0.0347239000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0265
_diffrn_reflns_av_unetI/netI     0.0376
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.895
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7512
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.895
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         30.252
_diffrn_reflns_theta_min         2.980
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.268
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94736
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            blue
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.465
_exptl_crystal_description       block
_exptl_crystal_F_000             924
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.541
_refine_diff_density_min         -0.907
_refine_diff_density_rms         0.089
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.48(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     395
_refine_ls_number_reflns         3809
_refine_ls_number_restraints     288
_refine_ls_restrained_S_all      1.156
_refine_ls_R_factor_all          0.0858
_refine_ls_R_factor_gt           0.0534
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.0661P)^2^+2.2592P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1324
_refine_ls_wR_factor_ref         0.1583
_reflns_Friedel_coverage         0.892
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.895
_reflns_number_gt                2616
_reflns_number_total             3809
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4cc09916h3.cif
_cod_data_source_block           gn1
_cod_database_code               7116795
_shelxl_version_number           2013-2
_chemical_oxdiff_formula         'C10 H10 N2 O2 Cl Cu'
_reflns_odcompleteness_completeness 99.73
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.50
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Shared sites
{N5, N5A}
3. Restrained distances
 C1-N2 = N5-C10 = C10-C11 = C11-N12 = N8-C8
 1.4 with sigma of 0.02
 Cl1A-O1A = Cl1A-O2A = Cl1A-O3A = Cl1A-O4A
 1.414 with sigma of 0.02
 Cl1B-O1B = Cl1B-O2B = Cl1B-O3B = Cl1B-O4B
 1.414 with sigma of 0.02
 O1A-O2A = O1A-O3A = O1A-O4A
 2.309 with sigma of 0.04
 O2A-O3A = O2A-O4A = O3A-O4A
 2.309 with sigma of 0.04
 O1B-O2B = O1B-O3B = O1B-O4B
 2.309 with sigma of 0.04
 O2B-O3B = O2B-O4B = O3B-O4B
 2.309 with sigma of 0.04
4. Uiso/Uaniso restraints and constraints
Cl1A \\sim O1A \\sim O2A \\sim O3A \\sim O4A: within 1.7A with sigma of 0.004
and sigma for terminal atoms of 0.008
Cl1B \\sim O1B \\sim O2B \\sim O3B \\sim O4B: within 1.7A with sigma of 0.008
and sigma for terminal atoms of 0.016
C1 \\sim C2 \\sim N2 \\sim C3 \\sim C4 \\sim C6 \\sim C7 \\sim N8 \\sim C8
\\sim C9 \\sim C10 \\sim C11 \\sim C12 \\sim N12 \\sim C13 \\sim O14: within
1.7A with sigma of 0.008 and sigma for terminal atoms of 0.016
C1A \\sim C2A \\sim N2A \\sim C3A \\sim C4A \\sim C6A \\sim C7A \\sim N8A \\sim
C8A \\sim C9A \\sim C10A \\sim C11A \\sim C12A \\sim N12A \\sim C13A: within
1.7A with sigma of 0.008 and sigma for terminal atoms of 0.016
Uanis(N12) \\sim Ueq, Uanis(N8A) \\sim Ueq, Uanis(O4A) \\sim Ueq: with sigma of
0.008 and sigma for terminal atoms of 0.016
Uanis(N2A) \\sim Ueq, Uanis(C4A) \\sim Ueq, Uanis(C6A) \\sim Ueq, Uanis(C7A)
\\sim Ueq, Uanis(C10A) \\sim Ueq, Uanis(C11A) \\sim Ueq, Uanis(N12A) \\sim Ueq,
Uanis(C10) \\sim Ueq, Uanis(O3A) \\sim Ueq: with sigma of 0.0008 and sigma for
terminal atoms of 0.0016
Uanis(C3) \\sim Ueq, Uanis(C4) \\sim Ueq, Uanis(C7) \\sim Ueq, Uanis(C6) \\sim
Ueq: with sigma of 0.008 and sigma for terminal atoms of 0.016
Uanis(N5) = Uanis(N5A)
5. Others
 Sof(Cl1B)=Sof(O1B)=Sof(O2B)=Sof(O3B)=Sof(O4B)=1-FVAR(1)
 Sof(Cl1A)=Sof(O1A)=Sof(O2A)=Sof(O3A)=Sof(O4A)=FVAR(1)
 Fixed Sof: C1(0.5) H1A(0.5) H1B(0.5) H1C(0.5) N2(0.5) C2(0.5) H2A(0.5)
 H2B(0.5) H2C(0.5) C3(0.5) H3A(0.5) H3B(0.5) C4(0.5) H4A(0.5) H4B(0.5) N5(0.5)
 C6(0.5) H6A(0.5) H6B(0.5) C7(0.5) H7A(0.5) H7B(0.5) N8(0.5) C8(0.5) H8A(0.5)
 H8B(0.5) H8C(0.5) C9(0.5) H9A(0.5) H9B(0.5) H9C(0.5) C10(0.5) H10A(0.5)
 H10B(0.5) C11(0.5) H11A(0.5) H11B(0.5) N12(0.5) C12(0.5) H12A(0.5) H12B(0.5)
 H12C(0.5) C13(0.5) H13A(0.5) H13B(0.5) H13C(0.5) C1A(0.5) H1AA(0.5) H1AB(0.5)
 H1AC(0.5) C2A(0.5) H2AA(0.5) H2AB(0.5) H2AC(0.5) N2A(0.5) C3A(0.5) H3AA(0.5)
 H3AB(0.5) C4A(0.5) H4AA(0.5) H4AB(0.5) N5A(0.5) C6A(0.5) H6AA(0.5) H6AB(0.5)
 C7A(0.5) H7AA(0.5) H7AB(0.5) N8A(0.5) C8A(0.5) H8AA(0.5) H8AB(0.5) H8AC(0.5)
 C9A(0.5) H9AA(0.5) H9AB(0.5) H9AC(0.5) C10A(0.5) H10C(0.5) H10D(0.5) C11A(0.5)
 H11C(0.5) H11D(0.5) C12A(0.5) H12D(0.5) H12E(0.5) H12F(0.5) N12A(0.5)
 C13A(0.5) H13D(0.5) H13E(0.5) H13F(0.5)
6.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B), C6(H6A,H6B), C7(H7A,H7B), C10(H10A,H10B), C11(H11A,
 H11B), C3A(H3AA,H3AB), C4A(H4AA,H4AB), C6A(H6AA,H6AB), C7A(H7AA,H7AB),
 C10A(H10C,H10D), C11A(H11C,H11D)
6.b Aromatic/amide H refined with riding coordinates:
 C15(H15)
6.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C2(H2A,H2B,H2C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C12(H12A,
 H12B,H12C), C13(H13A,H13B,H13C), C1A(H1AA,H1AB,H1AC), C2A(H2AA,H2AB,H2AC),
 C8A(H8AA,H8AB,H8AC), C9A(H9AA,H9AB,H9AC), C12A(H12D,H12E,H12F), C13A(H13D,H13E,
 H13F)
;
_olex2_submission_special_instructions 'No special instructions were received'