Crystal structure of methyl 2-(4-(2-(cyclopentyl-amino)-1-(N-(4-methoxyphenyl)-1-methyl-5-phenyl-1-H-pyrazole-3-carboxamido)-2-oxoethyl)phenyl)acetate, C34H36N4O5
Zhang, Youlu; Ma, Fengwei; Zhang, Bo; Mi, Xia; Zhang, Jingyu; Zeitschrift für Kristallographie - New Crystal Structures 237 (2022) 301–303; doi:10.1515/ncrs-2021-0458

data_8105210
_publ_section_title
;
 Crystal structure of methyl
 2-(4-(2-(cyclopentyl-amino)-1-(N-(4-methoxyphenyl)-1-methyl-5-phenyl-1-H-pyrazole-3-carboxamido)-2-oxoethyl)phenyl)acetate,
 C34H36N4O5
;
_journal_issue                   2
_journal_name_full
'Zeitschrift f\"ur Kristallographie - New Crystal Structures'
_journal_page_first              301
_journal_page_last               303
_journal_paper_doi               10.1515/ncrs-2021-0458
_journal_volume                  237
_journal_year                    2022
_chemical_formula_moiety         'C34 H36 N4 O5'
_chemical_formula_sum            'C34 H36 N4 O5'
_chemical_formula_weight         580.67
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_cell_angle_alpha                90
_cell_angle_beta                 132.845(5)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   29.9636(9)
_cell_length_b                   20.4000(3)
_cell_length_c                   14.2266(4)
_cell_measurement_reflns_used    11546
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.5110
_cell_measurement_theta_min      3.8760
_cell_volume                     6376.0(6)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_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  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w    -52.00  22.00   1.00    1.00    --    0.00 -37.00-150.00   74
  2  \w     -3.00  29.00   1.00    1.00    --    0.00 -84.00 176.00   32
  3  \w    -45.00  -7.00   1.00    2.50    --  -33.50 -77.00  30.00   38
  4  \w    -61.00  28.00   1.00    2.50    --  -33.50  77.00 -60.00   89
  5  \w   -103.00 -52.00   1.00    2.50    --  -33.50 -77.00  30.00   51
  6  \w   -102.00  -5.00   1.00    2.50    --  -33.50 -77.00-180.00   97
  7  \w     -9.00  16.00   1.00    2.50    --   36.47 108.00-129.87   25
  8  \w     59.00 106.00   1.00    2.50    --   36.47 178.00-180.00   47
  9  \w      6.00  76.00   1.00    2.50    --   36.47 -99.00-180.00   70
 10  \w     -1.00  77.00   1.00    2.50    --   36.47 -99.00  30.00   78
 11  \w     58.00 102.00   1.00    2.50    --   36.47 178.00 -60.00   44
 12  \w      0.00  25.00   1.00    2.50    --   40.00  98.00  32.69   25
 13  \w      7.00  32.00   1.00    2.50    --   44.00  92.00-139.07   25
 14  \w     13.00  38.00   1.00    2.50    --   48.00  88.00  55.90   25
 15  \w     13.00  38.00   1.00    2.50    --   48.00  88.00 -51.14   25
 16  \w     20.00  45.00   1.00    2.50    --   52.00  84.00-131.53   25
 17  \w     20.00  45.00   1.00    2.50    --   52.00  83.00 147.68   25
 18  \w     20.00  45.00   1.00    2.50    --   52.00  84.00  -7.95   25
 19  \w     20.00  45.00   1.00    2.50    --   52.00  84.00 -91.19   25
 20  \w     20.00  45.00   1.00    2.50    --   52.00  84.00  92.74   25
 21  \w     20.00  45.00   1.00    2.50    --   52.00  84.00-165.31   25
 22  \w     29.00  55.00   1.00    2.50    --   56.00  77.00  65.07   26
 23  \w     91.00 126.00   1.00    2.50    --   60.00  73.00 -35.00   35
 24  \w     32.00  63.00   1.00    2.50    --   60.00  75.00 151.34   31
 25  \w     70.00 127.00   1.00    2.50    --   60.00  68.00-108.81   57
 26  \w     32.00  58.00   1.00    2.50    --   60.00  76.00 -77.92   26
 27  \w     35.00  88.00   1.00    2.50    --   60.00  73.00 -35.00   53
 28  \w     91.00 129.00   1.00    2.50    --   60.00  79.00  19.24   38
 29  \w     32.00  74.00   1.00    2.50    --   60.00  75.00  98.68   42
 30  \w     83.00 128.00   1.00    2.50    --   60.00  70.00-168.37   45
 31  \w     30.00  74.00   1.00    2.50    --   60.00  79.00  19.24   44
 32  \w     38.00  64.00   1.00    2.50    --   60.00  68.00-108.81   26
 33  \w     35.00  67.00   1.00    2.50    --   60.00  70.00-168.37   32
 34  \w     98.00 128.00   1.00    2.50    --   60.00  76.00 -77.92   30
 35  \w     40.00  84.00   1.00    2.50    --   64.00  68.00 -54.11   44
 36  \w     96.00 134.00   1.00    2.50    --   68.00  63.00  67.89   38
 37  \w     47.00  86.00   1.00    2.50    --   68.00  63.00  67.89   39
 38  \w     53.00  88.00   1.00   11.50    --   76.00  67.00-146.82   35
 39  \w    106.00 151.00   1.00   11.50    --   84.00  57.00 117.27   45
 40  \w     65.00 101.00   1.00   11.50    --   84.00  57.00 117.27   36
 41  \w     88.00 173.00   1.00   11.50    --  108.00  61.00-120.00   85
 42  \w     88.00 130.00   1.00   11.50    --  108.00  61.00-150.00   42
 43  \w     67.00 110.00   1.00   11.50    --  108.00 -94.00 120.00   43
 44  \w     88.00 175.00   1.00   11.50    --  108.00  61.00-180.00   87
 45  \w     88.00 114.00   1.00   11.50    --  108.00  61.00  60.00   26
 46  \w     88.00 175.00   1.00   11.50    --  108.00  61.00 -30.00   87
 47  \w     79.00 164.00   1.00   11.50    --  108.00  77.00  90.00   85
 48  \w     88.00 122.00   1.00   11.50    --  108.00  61.00 -60.00   34
 49  \w    112.00 176.00   1.00   11.50    --  108.00  77.00 -60.00   64
 50  \w     88.00 165.00   1.00   11.50    --  108.00  61.00 -90.00   77
 51  \w     79.00 105.00   1.00   11.50    --  108.00  77.00 -60.00   26
 52  \w     88.00 176.00   1.00   11.50    --  108.00  61.00   0.00   88
 53  \w     80.00 106.00   1.00   11.50    --  108.00  77.00-180.00   26
 54  \w     45.00 112.00   1.00   11.50    --  108.00-111.00 -90.00   67
 55  \w     45.00 112.00   1.00   11.50    --  108.00-111.00   0.00   67
 56  \w     79.00 104.00   1.00   11.50    --  108.00  77.00 150.00   25
 57  \w     88.00 167.00   1.00   11.50    --  108.00  61.00 150.00   79
 58  \w     79.00 105.00   1.00   11.50    --  108.00  77.00 -30.00   26
 59  \w     38.00 106.00   1.00   11.50    --  108.00 -94.00  30.00   68
 60  \w    134.00 173.00   1.00   11.50    --  108.00  61.00-150.00   39
 61  \w     79.00 176.00   1.00   11.50    --  108.00  77.00  30.00   97
 62  \w     41.00 128.00   1.00   11.50    --  108.00 -61.00  30.00   87
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0213587500
_diffrn_orient_matrix_UB_12      0.0712618500
_diffrn_orient_matrix_UB_13      0.0446120000
_diffrn_orient_matrix_UB_21      -0.0511767500
_diffrn_orient_matrix_UB_22      0.0240452500
_diffrn_orient_matrix_UB_23      -0.1387683000
_diffrn_orient_matrix_UB_31      -0.0429095000
_diffrn_orient_matrix_UB_32      0.0067743000
_diffrn_orient_matrix_UB_33      0.0236689000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0416
_diffrn_reflns_av_unetI/netI     0.0199
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            41586
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.078
_diffrn_reflns_theta_max         67.078
_diffrn_reflns_theta_min         3.887
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.664
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86251
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
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    1.210
_exptl_crystal_description       block
_exptl_crystal_F_000             2464
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.374
_refine_diff_density_min         -0.305
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     424
_refine_ls_number_reflns         5692
_refine_ls_number_restraints     112
_refine_ls_restrained_S_all      1.152
_refine_ls_R_factor_all          0.0668
_refine_ls_R_factor_gt           0.0544
_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^)+(0.0973P)^2^+2.3056P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1597
_refine_ls_wR_factor_ref         0.1735
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4502
_reflns_number_total             5692
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            suppl_j_ncrs-2021-0458_suppl.cif
_cod_data_source_block           202111305
_cod_original_cell_volume        6376.0(5)
_cod_database_code               8105210
_chemical_oxdiff_formula         C30H3N1O4
_chemical_oxdiff_usercomment     r
_shelx_estimated_absorpt_t_max   0.937
_shelx_estimated_absorpt_t_min   0.895
_reflns_odcompleteness_completeness 99.68
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O5A-O4A
 2 with sigma of 0.02
 C31A-C32A
 1.58 with sigma of 0.02
 C30A-C34A
 1.54 with sigma of 0.02
 C30-C34
 1.54 with sigma of 0.02
 C32-C33
 1.58 with sigma of 0.02
 C33A-C34A
 1.54 with sigma of 0.02
 O5-C28
 1.4 with sigma of 0.02
 O5A-C28
 1.45 with sigma of 0.02
 C28-C27
 1.54 with sigma of 0.02
 O5A-C28A
 1.45 with sigma of 0.02
 O4A-C28A
 1.25 with sigma of 0.02
 O4-C28
 1.25 with sigma of 0.02
 C29-O5
 1.48 with sigma of 0.02
 C29A-O5A
 1.48 with sigma of 0.02
 C30A-C31A
 1.58 with sigma of 0.02
 C32A-C33A
 1.58 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C32A) \\sim Ueq, Uanis(C33) \\sim Ueq, Uanis(C33A) \\sim Ueq, Uanis(C32)
\\sim Ueq, Uanis(C31A) \\sim Ueq, Uanis(C31) \\sim Ueq, Uanis(C34) \\sim Ueq,
Uanis(C34A) \\sim Ueq, Uanis(C27) \\sim Ueq, Uanis(C27A) \\sim Ueq, Uanis(C30)
\\sim Ueq, Uanis(C30A) \\sim Ueq: with sigma of 0.01 and sigma for terminal
atoms of 0.02
Uanis(O4A) \\sim Ueq, Uanis(O4) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(C28A) \\sim Ueq, Uanis(C28) \\sim Ueq: with sigma of 0.008 and sigma for
terminal atoms of 0.008
Uanis(O4) = Uanis(O4A)
Uanis(O5) = Uanis(O5A)
Uanis(C30) = Uanis(C30A)
Uanis(C34) = Uanis(C34A)
Uanis(C33) = Uanis(C33A)
Uanis(C32) = Uanis(C32A)
Uanis(C31) = Uanis(C31A)
Uanis(C27) = Uanis(C27A)
Uanis(C28) = Uanis(C28A)
Uanis(C29) = Uanis(C29A)
4. Others
 Sof(O4A)=Sof(O5A)=1-FVAR(1)
 Sof(O4)=Sof(O5)=FVAR(1)
 Sof(C27A)=Sof(H27C)=Sof(H27D)=Sof(C28A)=Sof(C29A)=Sof(H29D)=Sof(H29E)=
 Sof(H29F)=Sof(C30A)=Sof(H30A)=Sof(C31A)=Sof(H31C)=Sof(H31D)=Sof(C32A)=
 Sof(H32C)=Sof(H32D)=Sof(C33A)=Sof(H33C)=Sof(H33D)=Sof(C34A)=Sof(H34C)=
 Sof(H34D)=Sof(H4B)=1-FVAR(2)
 Sof(C27)=Sof(H27A)=Sof(H27B)=Sof(C28)=Sof(C29)=Sof(H29A)=Sof(H29B)=Sof(H29C)=
 Sof(C30)=Sof(H30)=Sof(C31)=Sof(H31A)=Sof(H31B)=Sof(C32)=Sof(H32A)=Sof(H32B)=
 Sof(C33)=Sof(H33A)=Sof(H33B)=Sof(C34)=Sof(H34A)=Sof(H34B)=Sof(H4A)=FVAR(2)
5.a Ternary CH refined with riding coordinates:
 C12(H12), C30(H30), C30A(H30A)
5.b Secondary CH2 refined with riding coordinates:
 C27(H27A,H27B), C27A(H27C,H27D), C31(H31A,H31B), C31A(H31C,H31D), C32(H32A,
 H32B), C32A(H32C,H32D), C33(H33A,H33B), C33A(H33C,H33D), C34(H34A,H34B),
 C34A(H34C,H34D)
5.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C15(H15), C16(H16),
 C18(H18), C19(H19), C22(H22), C23(H23), C25(H25), C26(H26), N4(H4A), N4(H4B)
5.d Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C20(H20A,H20B,H20C), C29(H29A,H29B,H29C), C29A(H29D,H29E,H29F)
;