#------------------------------------------------------------------------------
#$Date: 2025-08-04 10:03:09 +0300 (Mon, 04 Aug 2025) $
#$Revision: 301442 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/05/67/7056741.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_7056741
loop_
_publ_author_name
'Cybularczyk, Martyna'
'Zaremba, Rafał'
'Hurko, Aleksander'
'Plichta, Andrzej Tadeusz'
'Dranka, Maciej'
'Horeglad, Paweł'
_publ_section_title
;
 Dialkylgallium alkoxides -- a tool for facile and stereoselective
 synthesis of PLA-drug conjugates
;
_journal_issue                   24
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              14851
_journal_page_last               14854
_journal_paper_doi               10.1039/C7NJ03089D
_journal_volume                  41
_journal_year                    2017
_chemical_formula_moiety         'C28 H48 Ga2 N2 O4'
_chemical_formula_sum            'C28 H48 Ga2 N2 O4'
_chemical_formula_weight         616.12
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2017-05-29
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2017-08-16 deposited with the CCDC.
2017-11-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.559(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   21.4049(7)
_cell_length_b                   8.2553(3)
_cell_length_c                   18.0932(5)
_cell_measurement_reflns_used    8135
_cell_measurement_temperature    293(1)
_cell_measurement_theta_max      30.1980
_cell_measurement_theta_min      3.8200
_cell_volume                     3143.00(18)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_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      293(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3347
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -48.00  64.00   1.00   22.50    --  -14.40  77.00  90.00  112
  2  ω    -93.00  19.00   1.00   22.50    --  -14.40 -77.00 -90.00  112
  3  ω    -88.00  15.00   1.00   22.50    --  -14.40 -57.00 -30.00  103
  4  ω    -61.00  41.00   1.00   22.50    --   14.72 -38.00  90.00  102
  5  ω    -44.00  16.00   1.00   22.50    --  -14.40  57.00 -60.00   60
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0062295000
_diffrn_orient_matrix_UB_12      -0.0570904000
_diffrn_orient_matrix_UB_13      -0.0297484000
_diffrn_orient_matrix_UB_21      0.0048850000
_diffrn_orient_matrix_UB_22      -0.0641848000
_diffrn_orient_matrix_UB_23      0.0264903000
_diffrn_orient_matrix_UB_31      -0.0327583000
_diffrn_orient_matrix_UB_32      0.0012759000
_diffrn_orient_matrix_UB_33      0.0020959000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0222
_diffrn_reflns_av_unetI/netI     0.0139
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            16888
_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         26.033
_diffrn_reflns_theta_min         3.259
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.746
_exptl_absorpt_correction_T_max  0.701
_exptl_absorpt_correction_T_min  0.462
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
            a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1296
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.414
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.241
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     170
_refine_ls_number_reflns         3096
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0269
_refine_ls_R_factor_gt           0.0221
_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/[σ²(Fo²)+(0.0320P)²+1.8530P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0584
_refine_ls_wR_factor_ref         0.0620
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2753
_reflns_number_total             3096
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c7nj03089d2.cif
_cod_data_source_block           md500_imp-ah-10
_cod_database_code               7056741
#BEGIN Tags that were not found in dictionaries:
_shelx_shelxl_version_number     2014/7
_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.
;
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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
Ga1 Ga 0.43412(2) 0.69097(2) 0.77437(2) 0.03490(8) Uani 1 1 d .
O1 O 0.46977(5) 0.72001(14) 0.68379(6) 0.0350(2) Uani 1 1 d .
O2 O 0.52721(6) 0.66502(16) 0.55626(7) 0.0477(3) Uani 1 1 d .
N1 N 0.33966(7) 0.6578(2) 0.66711(8) 0.0399(3) Uani 1 1 d .
H1 H 0.3378(9) 0.557(3) 0.6642(11) 0.048 Uiso 1 1 d R
C1 C 0.43640(7) 0.6617(2) 0.61421(9) 0.0353(3) Uani 1 1 d .
H1A H 0.4384 0.5431 0.6141 0.042 Uiso 1 1 calc R
C2 C 0.46421(8) 0.7260(2) 0.54907(9) 0.0402(4) Uani 1 1 d .
H2A H 0.4388 0.6909 0.5018 0.048 Uiso 1 1 calc R
H2B H 0.4647 0.8435 0.5499 0.048 Uiso 1 1 calc R
C3 C 0.36708(8) 0.7145(2) 0.60399(9) 0.0408(4) Uani 1 1 d .
H3A H 0.3644 0.8317 0.6010 0.049 Uiso 1 1 calc R
H3B H 0.3435 0.6700 0.5575 0.049 Uiso 1 1 calc R
C4 C 0.42131(9) 0.4617(2) 0.79670(11) 0.0518(5) Uani 1 1 d .
H4A H 0.4238 0.3974 0.7532 0.078 Uiso 1 1 calc GR
H4B H 0.3802 0.4481 0.8100 0.078 Uiso 1 1 calc GR
H4C H 0.4536 0.4277 0.8378 0.078 Uiso 1 1 calc GR
C5 C 0.40343(9) 0.8987(2) 0.80581(10) 0.0479(4) Uani 1 1 d .
H5A H 0.4390 0.9652 0.8270 0.072 Uiso 1 1 calc GR
H5B H 0.3773 0.8803 0.8428 0.072 Uiso 1 1 calc GR
H5C H 0.3790 0.9525 0.7630 0.072 Uiso 1 1 calc GR
C6 C 0.27670(9) 0.7242(3) 0.67155(12) 0.0540(5) Uani 1 1 d .
H6 H 0.2805 0.8424 0.6750 0.065 Uiso 1 1 calc R
C7 C 0.25621(11) 0.6645(3) 0.74172(13) 0.0684(6) Uani 1 1 d .
H7A H 0.2540 0.5484 0.7407 0.103 Uiso 1 1 calc GR
H7B H 0.2151 0.7081 0.7445 0.103 Uiso 1 1 calc GR
H7C H 0.2864 0.6989 0.7849 0.103 Uiso 1 1 calc GR
C8 C 0.22589(11) 0.6840(5) 0.60352(15) 0.1109(14) Uani 1 1 d .
H8A H 0.2351 0.7394 0.5601 0.166 Uiso 1 1 calc GR
H8B H 0.1851 0.7179 0.6127 0.166 Uiso 1 1 calc GR
H8C H 0.2254 0.5692 0.5948 0.166 Uiso 1 1 calc GR
C9 C 0.56243(9) 0.7113(2) 0.50396(10) 0.0450(4) Uani 1 1 d .
C10 C 0.62489(10) 0.6596(3) 0.51859(13) 0.0616(6) Uani 1 1 d .
H10 H 0.6406 0.6010 0.5619 0.074 Uiso 1 1 calc R
C11 C 0.66393(12) 0.6969(3) 0.46725(18) 0.0815(9) Uani 1 1 d .
H11 H 0.7060 0.6626 0.4763 0.098 Uiso 1 1 calc R
C12 C 0.64088(16) 0.7837(3) 0.40337(18) 0.0872(10) Uani 1 1 d .
H12 H 0.6673 0.8081 0.3694 0.105 Uiso 1 1 calc R
C13 C 0.57943(15) 0.8340(3) 0.38999(15) 0.0751(7) Uani 1 1 d .
H13 H 0.5642 0.8931 0.3467 0.090 Uiso 1 1 calc R
C14 C 0.53884(11) 0.7991(2) 0.43963(11) 0.0535(5) Uani 1 1 d .
H14 H 0.4968 0.8339 0.4299 0.064 Uiso 1 1 calc R
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'
Ga Ga 0.2307 1.6083 '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_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -12 -3 0.2080
-26 6 7 0.1447
-14 5 -18 0.1492
-20 1 -15 0.1051
2 -2 -25 0.2050
24 1 11 0.1533
27 -5 -7 0.1752
12 11 1 0.2486
0 11 -5 0.2259
-29 4 4 0.1393
2 -11 4 0.1858
-23 7 -3 0.1267
-23 -6 12 0.2145
5 -10 11 0.1742
-19 6 -11 0.1216
1 -8 18 0.1820
28 -4 2 0.1353
-22 4 -12 0.0954
16 -4 16 0.1232
-15 1 -19 0.1352
21 -1 15 0.1267
-15 -2 -19 0.1562
-23 1 20 0.1502
30 0 -6 0.1365
-17 -7 -11 0.1997
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_3
O1 Ga1 O1 77.11(5) 2_656
O1 Ga1 C4 112.52(7) .
O1 Ga1 C5 109.95(7) .
C4 Ga1 O1 101.71(7) 2_656
C5 Ga1 O1 98.98(6) 2_656
C5 Ga1 C4 135.81(9) .
Ga1 O1 Ga1 101.21(5) 2_656
C1 O1 Ga1 126.29(9) 2_656
C1 O1 Ga1 119.75(9) .
C9 O2 C2 118.10(14) .
C3 N1 H1 107.1(14) .
C3 N1 C6 115.39(15) .
C6 N1 H1 110.0(14) .
O1 C1 H1A 109.1 .
O1 C1 C2 111.59(13) .
O1 C1 C3 109.40(13) .
C2 C1 H1A 109.1 .
C2 C1 C3 108.57(13) .
C3 C1 H1A 109.1 .
O2 C2 C1 107.84(13) .
O2 C2 H2A 110.1 .
O2 C2 H2B 110.1 .
C1 C2 H2A 110.1 .
C1 C2 H2B 110.1 .
H2A C2 H2B 108.5 .
N1 C3 C1 109.67(14) .
N1 C3 H3A 109.7 .
N1 C3 H3B 109.7 .
C1 C3 H3A 109.7 .
C1 C3 H3B 109.7 .
H3A C3 H3B 108.2 .
Ga1 C4 H4A 109.5 .
Ga1 C4 H4B 109.5 .
Ga1 C4 H4C 109.5 .
H4A C4 H4B 109.5 .
H4A C4 H4C 109.5 .
H4B C4 H4C 109.5 .
Ga1 C5 H5A 109.5 .
Ga1 C5 H5B 109.5 .
Ga1 C5 H5C 109.5 .
H5A C5 H5B 109.5 .
H5A C5 H5C 109.5 .
H5B C5 H5C 109.5 .
N1 C6 H6 107.9 .
N1 C6 C7 109.68(17) .
N1 C6 C8 113.60(19) .
C7 C6 H6 107.9 .
C7 C6 C8 109.6(2) .
C8 C6 H6 107.9 .
C6 C7 H7A 109.5 .
C6 C7 H7B 109.5 .
C6 C7 H7C 109.5 .
H7A C7 H7B 109.5 .
H7A C7 H7C 109.5 .
H7B C7 H7C 109.5 .
C6 C8 H8A 109.5 .
C6 C8 H8B 109.5 .
C6 C8 H8C 109.5 .
H8A C8 H8B 109.5 .
H8A C8 H8C 109.5 .
H8B C8 H8C 109.5 .
O2 C9 C10 114.68(19) .
O2 C9 C14 124.41(18) .
C10 C9 C14 120.89(19) .
C9 C10 H10 120.6 .
C9 C10 C11 118.8(3) .
C11 C10 H10 120.6 .
C10 C11 H11 119.7 .
C12 C11 C10 120.7(3) .
C12 C11 H11 119.7 .
C11 C12 H12 120.1 .
C13 C12 C11 119.8(2) .
C13 C12 H12 120.1 .
C12 C13 H13 119.3 .
C12 C13 C14 121.4(3) .
C14 C13 H13 119.3 .
C9 C14 C13 118.5(2) .
C9 C14 H14 120.8 .
C13 C14 H14 120.8 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ga1 O1 1.9452(11) .
Ga1 O1 2.0717(11) 2_656
Ga1 C4 1.9648(18) .
Ga1 C5 1.9578(18) .
O1 Ga1 2.0717(11) 2_656
O1 C1 1.4134(18) .
O2 C2 1.423(2) .
O2 C9 1.368(2) .
N1 H1 0.83(2) .
N1 C3 1.454(2) .
N1 C6 1.471(2) .
C1 H1A 0.9800 .
C1 C2 1.511(2) .
C1 C3 1.525(2) .
C2 H2A 0.9700 .
C2 H2B 0.9700 .
C3 H3A 0.9700 .
C3 H3B 0.9700 .
C4 H4A 0.9600 .
C4 H4B 0.9600 .
C4 H4C 0.9600 .
C5 H5A 0.9600 .
C5 H5B 0.9600 .
C5 H5C 0.9600 .
C6 H6 0.9800 .
C6 C7 1.500(3) .
C6 C8 1.523(3) .
C7 H7A 0.9600 .
C7 H7B 0.9600 .
C7 H7C 0.9600 .
C8 H8A 0.9600 .
C8 H8B 0.9600 .
C8 H8C 0.9600 .
C9 C10 1.382(3) .
C9 C14 1.385(3) .
C10 H10 0.9300 .
C10 C11 1.393(3) .
C11 H11 0.9300 .
C11 C12 1.373(4) .
C12 H12 0.9300 .
C12 C13 1.358(4) .
C13 H13 0.9300 .
C13 C14 1.390(3) .
C14 H14 0.9300 .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
Ga1 O1 C1 C2 167.91(10) .
Ga1 O1 C1 C2 -57.85(17) 2_656
Ga1 O1 C1 C3 -178.01(10) 2_656
Ga1 O1 C1 C3 47.75(16) .
O1 C1 C2 O2 63.91(18) .
O1 C1 C3 N1 -56.45(18) .
O2 C9 C10 C11 178.14(18) .
O2 C9 C14 C13 -178.12(18) .
C2 O2 C9 C10 174.21(16) .
C2 O2 C9 C14 -7.5(3) .
C2 C1 C3 N1 -178.45(14) .
C3 N1 C6 C7 -176.21(18) .
C3 N1 C6 C8 60.7(3) .
C3 C1 C2 O2 -175.44(14) .
C6 N1 C3 C1 169.56(16) .
C9 O2 C2 C1 -178.40(14) .
C9 C10 C11 C12 0.2(3) .
C10 C9 C14 C13 0.1(3) .
C10 C11 C12 C13 0.0(4) .
C11 C12 C13 C14 -0.2(4) .
C12 C13 C14 C9 0.1(3) .
C14 C9 C10 C11 -0.2(3) .
