Crystal structure of methyl 2-(2-chloroacetyl)-1-(4-(methoxycarbonyl)phenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b] indole-3-carboxylate, C23H21ClN2O5
Xu, Xiaona; Zhu, Zhoujing; Liu, Bin; Zeitschrift für Kristallographie - New Crystal Structures 238 (2023) 355–357; doi:10.1515/ncrs-2022-0579

data_8107439
_publ_section_title
;
 Crystal structure of methyl
 2-(2-chloroacetyl)-1-(4-(methoxycarbonyl)phenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]
 indole-3-carboxylate, C23H21ClN2O5
;
_journal_issue                   2
_journal_name_full
'Zeitschrift f\"ur Kristallographie - New Crystal Structures'
_journal_page_first              355
_journal_page_last               357
_journal_paper_doi               10.1515/ncrs-2022-0579
_journal_volume                  238
_journal_year                    2023
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C23 H21 Cl N2 O5'
_chemical_formula_sum            'C23 H21 Cl N2 O5'
_chemical_formula_weight         440.87
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90
_cell_angle_beta                 109.869(13)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.191(3)
_cell_length_b                   10.725(5)
_cell_length_c                   11.2390(10)
_cell_measurement_reflns_used    81
_cell_measurement_temperature    173
_cell_measurement_theta_max      18.40
_cell_measurement_theta_min      2.71
_cell_volume                     1041.9(6)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      173.00
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0869
_diffrn_reflns_av_unetI/netI     0.1059
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11717
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         1.927
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.222
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.4215
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1383 before and 0.0813 after correction. The Ratio of minimum to maximum transmission is 0.5656. The \l/2 correction factor is 0.00150.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_description       block
_exptl_crystal_F_000             460
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.365
_refine_diff_density_min         -0.399
_refine_diff_density_rms         0.072
_refine_ls_abs_structure_details
;
 Flack x determined using 968 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.05(12)
_refine_ls_extinction_coef       0.020(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   0.982
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         4233
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.246
_refine_ls_R_factor_all          0.0951
_refine_ls_R_factor_gt           0.0609
_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^)+(0.0766P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1472
_refine_ls_wR_factor_ref         0.1695
_reflns_Friedel_coverage         0.884
_reflns_Friedel_fraction_full    0.992
_reflns_Friedel_fraction_max     0.988
_reflns_number_gt                2829
_reflns_number_total             4233
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            suppl_j_ncrs-2022-0579_suppl.cif
_cod_data_source_block           m
_cod_database_code               8107439
_shelx_estimated_absorpt_t_max   0.974
_shelx_estimated_absorpt_t_min   0.959
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 H11-H15B
 3 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C9(H9), C11(H11)
3.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C15(H15A,H15B)
3.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2A), C3(H3), C4(H4), C17(H17), C19(H19), C20(H20), C21(H21), N2(H2)
3.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C23(H23A,H23B,H23C)
;
_olex2_submission_special_instructions 'No special instructions were received'