#------------------------------------------------------------------------------
#$Date: 2025-08-04 09:03:09 +0200 (Mon 04 de Aug de 2025) $
#$Revision: 301442 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/67/7056742.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_7056742
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         'C14 H36 Ga2 N2 O2'
_chemical_formula_sum            'C14 H36 Ga2 N2 O2'
_chemical_formula_weight         403.89
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2017-05-28
_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                 95.288(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.4969(2)
_cell_length_b                   13.5023(4)
_cell_length_c                   11.1683(4)
_cell_measurement_reflns_used    6471
_cell_measurement_temperature    120.0(1)
_cell_measurement_theta_max      30.3790
_cell_measurement_theta_min      3.9380
_cell_volume                     975.55(5)
_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      120.0(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    -25.00  61.00   1.00    2.50    --  -14.40  38.00 120.00   86
  2  ω    -43.00  29.00   1.00    2.50    --  -14.40  57.00  30.00   72
  3  ω    -77.00 -51.00   1.00    2.50    --  -14.40 133.00  34.94   26
  4  ω    -93.00 -16.00   1.00    2.50    --  -14.40 156.00 121.31   77
  5  ω    -93.00 -16.00   1.00    2.50    --  -14.40 156.00-156.31   77
  6  ω    -88.00  13.00   1.00    2.50    --  -14.40 -57.00 -30.00  101
  7  ω    -90.00  12.00   1.00    2.50    --  -14.40 -38.00  60.00  102
  8  ω    -93.00  14.00   1.00    2.50    --  -14.40 -77.00-150.00  107
;
_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      0.0999420000
_diffrn_orient_matrix_UB_12      0.0187863000
_diffrn_orient_matrix_UB_13      0.0183737000
_diffrn_orient_matrix_UB_21      -0.0029295000
_diffrn_orient_matrix_UB_22      -0.0233532000
_diffrn_orient_matrix_UB_23      0.0566770000
_diffrn_orient_matrix_UB_31      0.0450255000
_diffrn_orient_matrix_UB_32      -0.0431678000
_diffrn_orient_matrix_UB_33      -0.0226836000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0438
_diffrn_reflns_av_unetI/netI     0.0231
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            15974
_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         27.874
_diffrn_reflns_theta_min         3.530
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.765
_exptl_absorpt_correction_T_max  0.683
_exptl_absorpt_correction_T_min  0.183
_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    1.375
_exptl_crystal_description       prism
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.892
_exptl_crystal_size_mid          0.382
_exptl_crystal_size_min          0.154
_refine_diff_density_max         0.322
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     98
_refine_ls_number_reflns         2331
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0244
_refine_ls_R_factor_gt           0.0206
_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)+(0.0220P)²+0.3500P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0508
_refine_ls_wR_factor_ref         0.0526
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2116
_reflns_number_total             2331
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c7nj03089d2.cif
_cod_data_source_block           md413_impuls_ah1
_cod_database_code               7056742
#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+1/2, y+1/2, -z+1/2'
'-x, -y, -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 0.50971(2) 0.60409(2) 0.56876(2) 0.01887(7) Uani 1 1 d .
O1 O 0.59238(19) 0.54201(8) 0.42704(11) 0.0316(3) Uani 1 1 d .
N1 N 0.69736(18) 0.73113(9) 0.48286(11) 0.0165(2) Uani 1 1 d D
H1 H 0.8391(16) 0.7248(12) 0.5179(14) 0.020 Uiso 1 1 d DR
C1 C 0.7243(3) 0.58884(11) 0.35291(15) 0.0258(3) Uani 1 1 d .
H1A H 0.6958 0.5646 0.2694 0.031 Uiso 1 1 calc R
H1B H 0.8697 0.5729 0.3805 0.031 Uiso 1 1 calc R
C2 C 0.6918(3) 0.69991(12) 0.35655(14) 0.0246(3) Uani 1 1 d .
H2A H 0.8019 0.7341 0.3168 0.029 Uiso 1 1 calc R
H2B H 0.5568 0.7173 0.3134 0.029 Uiso 1 1 calc R
C3 C 0.6345(2) 0.83536(10) 0.49854(14) 0.0199(3) Uani 1 1 d .
H3 H 0.4880 0.8426 0.4634 0.024 Uiso 1 1 calc R
C4 C 0.7007(3) 0.59770(12) 0.71608(17) 0.0300(4) Uani 1 1 d .
H4A H 0.6433 0.5538 0.7745 0.045 Uiso 1 1 calc GR
H4B H 0.7193 0.6642 0.7505 0.045 Uiso 1 1 calc GR
H4C H 0.8346 0.5719 0.6965 0.045 Uiso 1 1 calc GR
C5 C 0.2378(2) 0.67017(13) 0.54451(15) 0.0255(3) Uani 1 1 d .
H5A H 0.1937 0.6737 0.4583 0.038 Uiso 1 1 calc GR
H5B H 0.2487 0.7373 0.5779 0.038 Uiso 1 1 calc GR
H5C H 0.1361 0.6323 0.5853 0.038 Uiso 1 1 calc GR
C6 C 0.6421(3) 0.85797(12) 0.63196(15) 0.0278(4) Uani 1 1 d .
H6A H 0.5560 0.8102 0.6707 0.042 Uiso 1 1 calc GR
H6B H 0.5900 0.9251 0.6434 0.042 Uiso 1 1 calc GR
H6C H 0.7851 0.8532 0.6680 0.042 Uiso 1 1 calc GR
C7 C 0.7662(3) 0.90875(12) 0.43537(18) 0.0336(4) Uani 1 1 d .
H7A H 0.9121 0.8995 0.4641 0.050 Uiso 1 1 calc GR
H7B H 0.7239 0.9765 0.4530 0.050 Uiso 1 1 calc GR
H7C H 0.7474 0.8974 0.3484 0.050 Uiso 1 1 calc GR
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 15 10 0.2006
-2 -12 -11 0.2258
-8 3 -7 0.3723
-7 13 3 0.4155
1 13 -11 0.0804
0 -15 -10 0.1812
-1 -10 13 0.0768
-1 -14 11 0.0714
8 9 -5 0.2716
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 Ga1 O1 73.60(5) . 3_666
O1 Ga1 N1 151.09(4) 3_666 .
O1 Ga1 N1 77.70(4) . .
O1 Ga1 C4 117.98(7) . .
O1 Ga1 C5 113.62(6) . .
C4 Ga1 O1 96.73(6) . 3_666
C4 Ga1 N1 93.56(6) . .
C4 Ga1 C5 128.39(7) . .
C5 Ga1 O1 98.52(6) . 3_666
C5 Ga1 N1 96.03(6) . .
Ga1 O1 Ga1 106.40(5) . 3_666
C1 O1 Ga1 121.81(9) . .
C1 O1 Ga1 131.00(9) . 3_666
Ga1 N1 H1 106.1(10) . .
C2 N1 Ga1 102.35(8) . .
C2 N1 H1 107.5(10) . .
C2 N1 C3 113.81(12) . .
C3 N1 Ga1 118.98(9) . .
C3 N1 H1 107.4(10) . .
O1 C1 H1A 109.7 . .
O1 C1 H1B 109.7 . .
O1 C1 C2 109.72(13) . .
H1A C1 H1B 108.2 . .
C2 C1 H1A 109.7 . .
C2 C1 H1B 109.7 . .
N1 C2 C1 108.57(13) . .
N1 C2 H2A 110.0 . .
N1 C2 H2B 110.0 . .
C1 C2 H2A 110.0 . .
C1 C2 H2B 110.0 . .
H2A C2 H2B 108.4 . .
N1 C3 H3 108.0 . .
N1 C3 C6 108.85(12) . .
N1 C3 C7 112.98(13) . .
C6 C3 H3 108.0 . .
C6 C3 C7 110.78(13) . .
C7 C3 H3 108.0 . .
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 . .
C3 C6 H6A 109.5 . .
C3 C6 H6B 109.5 . .
C3 C6 H6C 109.5 . .
H6A C6 H6B 109.5 . .
H6A C6 H6C 109.5 . .
H6B C6 H6C 109.5 . .
C3 C7 H7A 109.5 . .
C3 C7 H7B 109.5 . .
C3 C7 H7C 109.5 . .
H7A C7 H7B 109.5 . .
H7A C7 H7C 109.5 . .
H7B C7 H7C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ga1 O1 1.9112(11) .
Ga1 O1 2.0831(11) 3_666
Ga1 N1 2.3589(12) .
Ga1 C4 1.9693(18) .
Ga1 C5 1.9754(16) .
O1 Ga1 2.0831(11) 3_666
O1 C1 1.3967(18) .
N1 H1 0.971(9) .
N1 C2 1.4696(19) .
N1 C3 1.4804(18) .
C1 H1A 0.9900 .
C1 H1B 0.9900 .
C1 C2 1.516(2) .
C2 H2A 0.9900 .
C2 H2B 0.9900 .
C3 H3 1.0000 .
C3 C6 1.517(2) .
C3 C7 1.524(2) .
C4 H4A 0.9800 .
C4 H4B 0.9800 .
C4 H4C 0.9800 .
C5 H5A 0.9800 .
C5 H5B 0.9800 .
C5 H5C 0.9800 .
C6 H6A 0.9800 .
C6 H6B 0.9800 .
C6 H6C 0.9800 .
C7 H7A 0.9800 .
C7 H7B 0.9800 .
C7 H7C 0.9800 .
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 -31.17(19) .
Ga1 O1 C1 C2 160.50(11) 3_666
Ga1 N1 C2 C1 -41.05(13) .
Ga1 N1 C3 C6 58.03(14) .
Ga1 N1 C3 C7 -178.47(11) .
O1 C1 C2 N1 49.07(18) .
C2 N1 C3 C6 178.81(13) .
C2 N1 C3 C7 -57.69(17) .
C3 N1 C2 C1 -170.76(12) .
