#------------------------------------------------------------------------------
#$Date: 2019-11-07 22:09:35 +0200 (Thu, 07 Nov 2019) $
#$Revision: 223716 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/33/7233302.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7233302
loop_
_publ_author_name
'Weekes, Rohan J.'
'Hawes, Chris S.'
_publ_section_title
;
 Synthesis, coordination chemistry and photophysical properties of
 naphtho-fused pyrazole ligands
;
_journal_issue                   34
_journal_name_full               CrystEngComm
_journal_page_first              5152
_journal_paper_doi               10.1039/C9CE01074B
_journal_volume                  21
_journal_year                    2019
_chemical_formula_moiety         'C44 H32 Cu N10 O6'
_chemical_formula_sum            'C44 H32 Cu N10 O6'
_chemical_formula_weight         860.33
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-06-20
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-07-06 deposited with the CCDC.    2019-08-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.1810(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.0209(3)
_cell_length_b                   21.4464(6)
_cell_length_c                   11.1543(3)
_cell_measurement_reflns_used    8775
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      30.64
_cell_measurement_theta_min      2.74
_cell_volume                     1899.23(10)
_computing_cell_refinement       'SAINT V8.38A (2016)'
_computing_data_reduction        'SAINT V8.38A (2016)'
_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      150.0
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0496
_diffrn_reflns_av_unetI/netI     0.0403
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            25442
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.635
_diffrn_reflns_theta_min         2.648
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.642
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6677
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0571 before and 0.0520 after correction. The Ratio of minimum to maximum transmission is 0.8949. The λ/2 correction factor is 0.00150.'
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.504
_exptl_crystal_description       rod
_exptl_crystal_F_000             886
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.536
_refine_diff_density_min         -0.509
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         5848
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0627
_refine_ls_R_factor_gt           0.0447
_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/[σ²(Fo²)+(0.0352P)²+1.7178P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0932
_refine_ls_wR_factor_ref         0.0995
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4670
_reflns_number_total             5848
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9ce01074b2.cif
_cod_data_source_block           1
_cod_depositor_comments
'Adding full bibliography for 7233301--7233306.cif.'
_cod_database_code               7233302
_shelx_shelxl_version_number     2017/1
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.944
_shelx_estimated_absorpt_t_min   0.779
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 N2-H2 = N4-H4
 0.88 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C4(H4A), C6(H6), C7(H7), C8(H8), C9(H9), C12(H12), C14(H14),
 C15(H15), C17(H17), C18(H18), C19(H19), C20(H20)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
Cu1 Cu 0.500000 0.500000 0.500000 0.01046(7) Uani 1 2 d S T P
O1 O 0.23615(16) 0.47088(7) 0.54859(13) 0.0231(3) Uani 1 1 d . . .
O2 O 0.05153(17) 0.44064(7) 0.39784(13) 0.0220(3) Uani 1 1 d . . .
O3 O 0.02097(19) 0.41516(7) 0.57988(13) 0.0266(3) Uani 1 1 d . . .
N1 N 0.53857(18) 0.41621(7) 0.42230(13) 0.0140(3) Uani 1 1 d . . .
N2 N 0.69002(18) 0.38723(7) 0.42807(14) 0.0144(3) Uani 1 1 d D . .
N3 N 0.40471(17) 0.53506(7) 0.33828(13) 0.0129(3) Uani 1 1 d . . .
N4 N 0.24025(18) 0.52768(7) 0.29110(13) 0.0133(3) Uani 1 1 d D . .
N5 N 0.10413(18) 0.44176(7) 0.50947(14) 0.0153(3) Uani 1 1 d . . .
C1 C 0.4287(2) 0.38202(8) 0.34989(16) 0.0162(3) Uani 1 1 d . . .
H1 H 0.311862 0.390910 0.331026 0.019 Uiso 1 1 calc R . .
C2 C 0.5105(2) 0.33056(8) 0.30500(16) 0.0159(3) Uani 1 1 d . . .
C3 C 0.4592(2) 0.28220(9) 0.21964(18) 0.0210(4) Uani 1 1 d . . .
H3 H 0.344832 0.278158 0.184163 0.025 Uiso 1 1 calc R . .
C4 C 0.5780(3) 0.24227(9) 0.19064(18) 0.0216(4) Uani 1 1 d . . .
H4A H 0.546088 0.210862 0.131785 0.026 Uiso 1 1 calc R . .
C5 C 0.7514(2) 0.24592(8) 0.24624(17) 0.0175(3) Uani 1 1 d . . .
C6 C 0.8719(3) 0.20322(9) 0.21497(19) 0.0232(4) Uani 1 1 d . . .
H6 H 0.838897 0.172549 0.154818 0.028 Uiso 1 1 calc R . .
C7 C 1.0359(3) 0.20532(9) 0.2701(2) 0.0264(4) Uani 1 1 d . . .
H7 H 1.115533 0.176406 0.247374 0.032 Uiso 1 1 calc R . .
C8 C 1.0867(3) 0.24992(9) 0.3597(2) 0.0254(4) Uani 1 1 d . . .
H8 H 1.199824 0.250468 0.398962 0.031 Uiso 1 1 calc R . .
C9 C 0.9729(2) 0.29296(9) 0.39112(19) 0.0201(4) Uani 1 1 d . . .
H9 H 1.008022 0.323231 0.451646 0.024 Uiso 1 1 calc R . .
C10 C 0.8051(2) 0.29225(8) 0.33394(17) 0.0154(3) Uani 1 1 d . . .
C11 C 0.6781(2) 0.33562(8) 0.35769(16) 0.0141(3) Uani 1 1 d . . .
C12 C 0.4735(2) 0.57195(8) 0.26271(16) 0.0162(3) Uani 1 1 d . . .
H12 H 0.587881 0.585006 0.273562 0.019 Uiso 1 1 calc R . .
C13 C 0.3517(2) 0.58876(9) 0.16429(16) 0.0166(3) Uani 1 1 d . . .
C14 C 0.3506(3) 0.62667(10) 0.05911(18) 0.0234(4) Uani 1 1 d . . .
H14 H 0.449973 0.647020 0.042540 0.028 Uiso 1 1 calc R . .
C15 C 0.2032(3) 0.63282(10) -0.01666(18) 0.0253(4) Uani 1 1 d . . .
H15 H 0.201099 0.657940 -0.087004 0.030 Uiso 1 1 calc R . .
C16 C 0.0503(3) 0.60281(9) 0.00544(17) 0.0211(4) Uani 1 1 d . . .
C17 C -0.1022(3) 0.61037(11) -0.07449(18) 0.0278(5) Uani 1 1 d . . .
H17 H -0.103712 0.635511 -0.144750 0.033 Uiso 1 1 calc R . .
C18 C -0.2469(3) 0.58203(11) -0.05198(19) 0.0293(5) Uani 1 1 d . . .
H18 H -0.347789 0.587779 -0.106754 0.035 Uiso 1 1 calc R . .
C19 C -0.2489(2) 0.54465(10) 0.05058(18) 0.0246(4) Uani 1 1 d . . .
H19 H -0.350416 0.525113 0.065034 0.030 Uiso 1 1 calc R . .
C20 C -0.1032(2) 0.53624(9) 0.13058(17) 0.0193(4) Uani 1 1 d . . .
H20 H -0.104302 0.511047 0.200515 0.023 Uiso 1 1 calc R . .
C21 C 0.0468(2) 0.56487(9) 0.10876(16) 0.0166(3) Uani 1 1 d . . .
C22 C 0.2039(2) 0.55940(8) 0.18631(15) 0.0140(3) Uani 1 1 d . . .
H4 H 0.177(3) 0.5044(9) 0.3282(19) 0.017 Uiso 1 1 d DR . .
H2 H 0.779(2) 0.4040(10) 0.4613(19) 0.017 Uiso 1 1 d DR . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
O1 Cu1 O1 180.0 3_666 .
N1 Cu1 O1 86.55(6) 3_666 .
N1 Cu1 O1 93.45(6) . .
N1 Cu1 O1 93.45(6) 3_666 3_666
N1 Cu1 O1 86.55(6) . 3_666
N1 Cu1 N1 180.0 3_666 .
N3 Cu1 O1 93.84(5) 3_666 3_666
N3 Cu1 O1 86.16(5) 3_666 .
N3 Cu1 O1 93.84(5) . .
N3 Cu1 O1 86.16(5) . 3_666
N3 Cu1 N1 90.54(6) 3_666 3_666
N3 Cu1 N1 90.55(6) . .
N3 Cu1 N1 89.45(6) . 3_666
N3 Cu1 N1 89.45(6) 3_666 .
N3 Cu1 N3 180.0 3_666 .
N5 O1 Cu1 143.00(12) . .
N2 N1 Cu1 124.92(11) . .
C1 N1 Cu1 128.15(12) . .
C1 N1 N2 106.73(14) . .
N1 N2 H2 121.7(15) . .
C11 N2 N1 110.98(14) . .
C11 N2 H2 126.4(15) . .
N4 N3 Cu1 122.03(11) . .
C12 N3 Cu1 130.82(12) . .
C12 N3 N4 106.93(14) . .
N3 N4 H4 119.4(15) . .
C22 N4 N3 110.84(14) . .
C22 N4 H4 129.8(15) . .
O1 N5 O2 120.16(15) . .
O3 N5 O1 120.86(16) . .
O3 N5 O2 118.94(15) . .
N1 C1 H1 124.9 . .
N1 C1 C2 110.22(16) . .
C2 C1 H1 124.9 . .
C1 C2 C3 134.41(17) . .
C11 C2 C1 105.00(15) . .
C11 C2 C3 120.47(17) . .
C2 C3 H3 120.9 . .
C4 C3 C2 118.22(18) . .
C4 C3 H3 120.9 . .
C3 C4 H4A 119.0 . .
C3 C4 C5 122.09(17) . .
C5 C4 H4A 119.0 . .
C6 C5 C4 120.75(18) . .
C6 C5 C10 118.27(18) . .
C10 C5 C4 120.98(16) . .
C5 C6 H6 119.5 . .
C7 C6 C5 121.02(19) . .
C7 C6 H6 119.5 . .
C6 C7 H7 119.8 . .
C6 C7 C8 120.32(18) . .
C8 C7 H7 119.8 . .
C7 C8 H8 119.9 . .
C9 C8 C7 120.19(19) . .
C9 C8 H8 119.9 . .
C8 C9 H9 119.9 . .
C8 C9 C10 120.24(19) . .
C10 C9 H9 119.9 . .
C5 C10 C11 115.36(16) . .
C9 C10 C5 119.89(16) . .
C9 C10 C11 124.75(17) . .
N2 C11 C2 107.05(15) . .
N2 C11 C10 130.19(16) . .
C2 C11 C10 122.74(16) . .
N3 C12 H12 125.0 . .
N3 C12 C13 109.95(15) . .
C13 C12 H12 125.0 . .
C12 C13 C14 135.18(18) . .
C22 C13 C12 105.07(15) . .
C22 C13 C14 119.74(17) . .
C13 C14 H14 121.0 . .
C15 C14 C13 118.06(19) . .
C15 C14 H14 121.0 . .
C14 C15 H15 118.7 . .
C14 C15 C16 122.56(18) . .
C16 C15 H15 118.7 . .
C17 C16 C15 121.48(18) . .
C21 C16 C15 120.91(17) . .
C21 C16 C17 117.61(19) . .
C16 C17 H17 119.5 . .
C18 C17 C16 120.93(19) . .
C18 C17 H17 119.5 . .
C17 C18 H18 119.5 . .
C17 C18 C19 120.95(19) . .
C19 C18 H18 119.5 . .
C18 C19 H19 120.1 . .
C20 C19 C18 119.8(2) . .
C20 C19 H19 120.1 . .
C19 C20 H20 120.0 . .
C19 C20 C21 119.99(19) . .
C21 C20 H20 120.0 . .
C16 C21 C22 115.03(17) . .
C20 C21 C16 120.67(17) . .
C20 C21 C22 124.30(17) . .
N4 C22 C13 107.21(15) . .
N4 C22 C21 129.08(16) . .
C13 C22 C21 123.71(16) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 O1 2.3429(13) .
Cu1 O1 2.3429(13) 3_666
Cu1 N1 2.0377(15) .
Cu1 N1 2.0376(15) 3_666
Cu1 N3 2.0027(14) 3_666
Cu1 N3 2.0027(14) .
O1 N5 1.2531(19) .
O2 N5 1.257(2) .
O3 N5 1.240(2) .
N1 N2 1.358(2) .
N1 C1 1.328(2) .
N2 C11 1.352(2) .
N2 H2 0.841(15) .
N3 N4 1.3582(19) .
N3 C12 1.332(2) .
N4 C22 1.348(2) .
N4 H4 0.860(16) .
C1 H1 0.9500 .
C1 C2 1.412(2) .
C2 C3 1.428(2) .
C2 C11 1.392(2) .
C3 H3 0.9500 .
C3 C4 1.354(3) .
C4 H4A 0.9500 .
C4 C5 1.442(3) .
C5 C6 1.411(3) .
C5 C10 1.418(2) .
C6 H6 0.9500 .
C6 C7 1.371(3) .
C7 H7 0.9500 .
C7 C8 1.402(3) .
C8 H8 0.9500 .
C8 C9 1.378(3) .
C9 H9 0.9500 .
C9 C10 1.405(3) .
C10 C11 1.432(2) .
C12 H12 0.9500 .
C12 C13 1.409(2) .
C13 C14 1.426(3) .
C13 C22 1.395(3) .
C14 H14 0.9500 .
C14 C15 1.358(3) .
C15 H15 0.9500 .
C15 C16 1.437(3) .
C16 C17 1.416(3) .
C16 C21 1.414(3) .
C17 H17 0.9500 .
C17 C18 1.365(3) .
C18 H18 0.9500 .
C18 C19 1.399(3) .
C19 H19 0.9500 .
C19 C20 1.377(3) .
C20 H20 0.9500 .
C20 C21 1.402(3) .
C21 C22 1.428(2) .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N4 H4 O2 0.860(16) 1.925(16) 2.776(2) 170(2) . yes
N2 H2 O3 0.841(15) 2.197(17) 2.999(2) 159(2) 1_655 yes
